| 2020-05-19 18:00:5919/05/2020 | Huntington Rovers Ladies  | 2 - 8 |  Guisborough Town Ladies | North Riding Womens Premier League | |
| 2020-09-05 13:30:0005/09/2020 | Guisborough Town U18 | 2 - 3 | | Durham County FA U18s Saturday League | |
| 2020-09-05 15:00:0005/09/2020 | Stockton Town  | 2 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2020-09-06 14:00:0006/09/2020 | Guisborough Town Ladies | 14:00:00Postponed | Brompton Ladies | North Riding Womens Premier League | |
| 2020-09-09 19:45:0009/09/2020 | Guisborough Town | 5 - 1 |  West Auckland Town | Ebac Northern League Division 1 | |
| 2020-09-12 13:30:0012/09/2020 | Guisborough Town U18 | 0 - 6 |  New Hartley | Durham County FA U18s Saturday League | |
| 2020-09-12 15:00:0012/09/2020 | Guisborough Town | 1 - 2 |  Tadcaster Albion | Emirates FA Cup | |
| 2020-09-16 19:30:0016/09/2020 | Whickham  | 3 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2020-09-19 13:30:0019/09/2020 | Norton & Stockton Ancients | 5 - 1 | Guisborough Town U18 | Durham County FA U18s Saturday League | |
| 2020-09-19 15:00:0019/09/2020 | Guisborough Town | 3 - 0 |  Washington | Buildbase FA Vase | |
| 2020-09-20 14:00:0020/09/2020 | Huntington Rovers Ladies | 14:00:00Postponed | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2020-09-23 19:45:0023/09/2020 | Guisborough Town | 2 - 4 |  North Shields | Ebac Northern League Division 1 | |
| 2020-09-26 15:00:0026/09/2020 | Penrith  | 2 - 4 | Guisborough Town | Ebac Northern League Division 1 | |
| 2020-09-27 14:00:0627/09/2020 | Blyth Ladies | 7 - 1 | Guisborough Town Ladies | Adobe Women's FA Cup | |
| 2020-09-27 14:05:0027/09/2020 | Guisborough Town Ladies | 14:05:00Postponed |  Poppleton Ladies | North Riding Womens Premier League | |
| 2020-09-30 15:00:0030/09/2020 | Bishop Auckland  | 2 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2020-10-02 19:30:0002/10/2020 | Darlington R.A.  | 6 - 0 | Guisborough Town U18 | Durham County FA U18s Saturday League | |
| 2020-10-03 15:00:0003/10/2020 | Guisborough Town | 1 - 2 |  Ashington | Ebac Northern League Division 1 | |
| 2020-10-04 14:00:0004/10/2020 | Redcar Athletic Ladies  | 2 - 2 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2020-10-07 19:45:0007/10/2020 | Guisborough Town | 1 - 1 |  Newton Aycliffe | Ebac Northern League Division 1 | |
| 2020-10-10 15:00:0010/10/2020 | Silsden AFC  | 3 - 5 | Guisborough Town | Buildbase FA Vase | |
| 2020-10-10 15:00:0010/10/2020 | Guisborough Town | 1 - 0 | Newton Aycliffe | Emirates FA Cup | |
| 2020-10-11 11:00:0411/10/2020 | | 4 - 4 | | North Riding U15 County Cup | |
| 2020-10-11 14:00:0011/10/2020 | Guisborough Town Ladies | 14:00:0014:00 |  York St. John University Women’s | North Riding Womens Premier League | |
| 2020-10-11 14:00:0411/10/2020 | Guisborough Town Ladies | 8 - 0 |  Richmond Town Women | North Riding Womens Premier League | |
| 2020-10-14 19:45:0014/10/2020 | Guisborough Town | 1 - 2 |  Thornaby | Ebac Northern League Division 1 | |
| 2020-10-17 13:30:0017/10/2020 | Guisborough Town U18 | 12 - 0 | | Durham County FA U18s Saturday League | |
| 2020-10-17 15:00:0017/10/2020 | Newcastle Benfield  | 6 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2020-10-18 14:00:0018/10/2020 | Richmond Town Women | 1 - 6 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2020-10-24 15:00:0024/10/2020 | Guisborough Town | 0 - 5 |  Whitley Bay | Ebac Northern League Division 1 | |
| 2020-10-25 13:30:2625/10/2020 | | 8 - 1 | | North Riding U16 County Cup | |
| 2020-10-25 14:00:0025/10/2020 | Guisborough Town Ladies | 14:00:00Postponed | | North Riding Womens Premier League | |
| 2020-10-27 19:30:0027/10/2020 | Sunderland RCA  | 5 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2020-10-31 15:00:0031/10/2020 | Guisborough Town | 2 - 0 |  Runcorn Town | Buildbase FA Vase | |
| 2020-11-01 14:00:0001/11/2020 | Redcar Town Ladies Reserves  | 0 - 0 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2020-11-15 14:00:0015/11/2020 | Brompton Ladies | 14:00:0014:00 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2020-11-29 14:00:0029/11/2020 | Guisborough Town Ladies | 14:00:0014:00 | Huntington Rovers Ladies | North Riding Womens Premier League | |
| 2020-12-05 13:30:0005/12/2020 | Guisborough Town | 1 - 4 | Liversedge F.C. | Buildbase FA Vase | |
| 2020-12-06 14:00:0006/12/2020 | Poppleton Ladies | 14:00:0014:00 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2020-12-13 13:30:2713/12/2020 | | 0 - 8 | | North Riding U14 County Cup | |
| 2020-12-13 13:30:4913/12/2020 | | 13:30:4913:30 | | North Riding U15 County Cup | |
| 2020-12-13 14:00:0013/12/2020 | Guisborough Town Ladies | 14:00:00Postponed | York St. John University Women’s | North Riding Womens Premier League | |
| 2020-12-20 13:30:2320/12/2020 | | H - W | | North Riding U16 County Cup | |
| 2021-04-02 18:15:0002/04/2021 | Guisborough Town Over 35s  | 2 - 1 | TS3 | Celestial Windows Middlesbrough Over 35 League | |
| 2021-04-03 13:30:0003/04/2021 | Redcar Athletic | 5 - 1 | Guisborough Town U18 | Durham County FA U18s Saturday League | |
| 2021-04-04 14:00:0004/04/2021 | Guisborough Town Ladies | 7 - 1 | Brompton Ladies | North Riding Womens Premier League | |
| 2021-04-09 18:15:0009/04/2021 | Guisborough Town Over 35s | 6 - 0 | | Celestial Windows Middlesbrough Over 35 League | |
| 2021-04-11 14:00:1011/04/2021 | Redcar Athletic Ladies | 2 - 2 | Guisborough Town Ladies | North Riding Womens Cup | |
| 2021-04-14 18:00:0014/04/2021 | Guisborough Town Ladies | 18:00:00Postponed | Redcar Athletic Ladies | North Riding Womens Premier League | |
| 2021-04-16 18:15:0016/04/2021 | Guisborough Town Over 35s | 3 - 3 | Stockton Town Vets | Celestial Windows Middlesbrough Over 35 League | |
| 2021-04-17 13:30:0017/04/2021 | Guisborough Town U18 | 1 - 3 | Newcastle Benfield | Durham County FA U18s Saturday League | |
| 2021-04-18 14:00:0018/04/2021 | Brompton Ladies | 1 - 9 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2021-04-21 18:00:0021/04/2021 | Guisborough Town Ladies | 0 - 1 | Redcar Town Ladies Reserves | North Riding Womens Premier League | |
| 2021-04-23 18:15:0023/04/2021 | Thornaby FC Vets | 3 - 3 | Guisborough Town Over 35s | Celestial Windows Middlesbrough Over 35 League | |
| 2021-04-24 13:30:0024/04/2021 | Guisborough Town U18 | 0 - 8 | Billingham Town | Durham County FA U18s Saturday League | |
| 2021-04-25 14:00:4425/04/2021 | York RI Ladies  | 8 - 4 | Guisborough Town Ladies | North Riding Womens Cup | |
| 2021-04-29 14:00:0029/04/2021 | Guisborough Town Ladies | 6 - 0 | Redcar Athletic Ladies | North Riding Womens Premier League | |
| 2021-04-30 18:15:0030/04/2021 | Guisborough Town Over 35s | 0 - 1 | Brotton Railway Arms | Celestial Windows Middlesbrough Over 35 League | |
| 2021-05-02 14:00:0002/05/2021 | Guisborough Town Ladies | 1 - 1 | Poppleton Ladies | North Riding Womens Premier League | |
| 2021-05-07 18:15:0007/05/2021 | Coulby Newham | 2 - 2 | Guisborough Town Over 35s | Celestial Windows Middlesbrough Over 35 League | |
| 2021-05-07 18:30:0007/05/2021 | Guisborough Town U18 | 1 - 5 | | Durham County FA U18s Saturday League | |
| 2021-05-09 13:30:3509/05/2021 | | 1 - 2 | | North Riding U16 County Cup | |
| 2021-05-09 14:00:0009/05/2021 | Guisborough Town Ladies | 7 - 2 | York St. John University Women’s | North Riding Womens Premier League | |
| 2021-05-14 18:15:0014/05/2021 | Guisborough Town Over 35s | 1 - 4 | Darlington RA Vets | Celestial Windows Middlesbrough Over 35 League | |
| 2021-05-16 14:00:0016/05/2021 | Guisborough Town Ladies | 9 - 1 | Huntington Rovers Ladies | North Riding Womens Premier League | |
| 2021-05-18 18:30:2918/05/2021 | | 0 - 4 | | North Riding U16 County Cup | |
| 2021-05-21 18:15:0021/05/2021 | Dormans Vets | 2 - 0 | Guisborough Town Over 35s | Celestial Windows Middlesbrough Over 35 League | |
| 2021-05-22 13:30:0022/05/2021 | Guisborough Town U18 | 2 - 4 |  Darlington FC | Durham County FA U18s Saturday League | |
| 2021-05-23 14:00:0023/05/2021 | York St. John University Women’s | 2 - 7 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2021-05-25 18:30:5325/05/2021 | | 0 - 5 | | North Riding Junior Girls Cup – U16 | |
| 2021-05-28 18:15:0028/05/2021 | Guisborough Town Over 35s | 0 - 5 | George & Dragon Vets 1 | Celestial Windows Middlesbrough Over 35 League | |
| 2021-05-30 14:00:0030/05/2021 | Poppleton Ladies | 1 - 3 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2021-06-04 18:15:0004/06/2021 | Whinney Banks Vets | 5 - 2 | Guisborough Town Over 35s | Celestial Windows Middlesbrough Over 35 League | |
| 2021-06-11 18:15:0011/06/2021 | Hartlepool FC | 5 - 2 | Guisborough Town Over 35s | Celestial Windows Middlesbrough Over 35 League | |
| 2021-06-18 18:15:0018/06/2021 | Guisborough Town Over 35s | 1 - 6 | Hartlepool FC | Celestial Windows Middlesbrough Over 35 League | |
| 2021-06-25 18:15:0025/06/2021 | TS3 | 2 - 4 | Guisborough Town Over 35s | Celestial Windows Middlesbrough Over 35 League | |
| 2021-06-26 14:30:0926/06/2021 | Guisborough Town | 0 - 4 | | Friendly | |
| 2021-06-30 18:30:4730/06/2021 | Guisborough Town | C - C | | Friendly | |
| 2021-07-03 15:00:0403/07/2021 | Northallerton Town  | C - C | Guisborough Town | Friendly | |
| 2021-07-09 18:15:0009/07/2021 | Stockton Town Vets | 3 - 1 | Guisborough Town Over 35s | Celestial Windows Middlesbrough Over 35 League | |
| 2021-07-10 15:00:1710/07/2021 | Stockton Town | 3 - 0 | Guisborough Town | Friendly | |
| 2021-07-14 19:30:1214/07/2021 | Guisborough Town | 0 - 5 |  Marske United | John Butterfield Memorial Trophy | |
| 2021-07-16 18:15:0016/07/2021 | Guisborough Town Over 35s | 3 - 2 | Thornaby FC Vets | Celestial Windows Middlesbrough Over 35 League | |
| 2021-07-17 15:00:1417/07/2021 | Thornaby | 2 - 0 | Guisborough Town | Peter Morris Memorial Trophy | |
| 2021-07-20 19:30:0220/07/2021 | Guisborough Town | C - C |  Whitby Town | Micky Skinner Memorial Trophy | |
| 2021-07-23 18:15:0023/07/2021 | Brotton Railway Arms | 3 - 1 | Guisborough Town Over 35s | Celestial Windows Middlesbrough Over 35 League | |
| 2021-07-24 12:30:4724/07/2021 | Redcar Town | 4 | Guisborough Town | Mo Mowlam Memorial Cup | |
| 2021-07-25 15:00:0925/07/2021 | Marske United | 2 - 0 | Guisborough Town | Mo Mowlam Memorial Cup | |
| 2021-07-30 18:15:0030/07/2021 | Guisborough Town Over 35s | 1 - 5 | Coulby Newham | Celestial Windows Middlesbrough Over 35 League | |
| 2021-07-31 15:00:0031/07/2021 | Guisborough Town | 0 - 1 | Bishop Auckland | Ebac Northern League Division 1 | |
| 2021-08-04 19:45:0004/08/2021 | Guisborough Town | 2 - 0 | Sunderland RCA | Ebac Northern League Division 1 | |
| 2021-08-06 18:15:0006/08/2021 | Darlington RA Vets | 3 - 0 | Guisborough Town Over 35s | Celestial Windows Middlesbrough Over 35 League | |
| 2021-08-07 15:00:5407/08/2021 | Penrith | 1 - 2 | Guisborough Town | Emirates FA Cup | |
| 2021-08-11 19:45:0011/08/2021 | Guisborough Town | 0 - 2 | Ashington | Ebac Northern League Division 1 | |
| 2021-08-13 18:15:0013/08/2021 | Guisborough Town Over 35s | 2 - 2 | Dormans Vets | Celestial Windows Middlesbrough Over 35 League | |
| 2021-08-14 15:00:0014/08/2021 | Guisborough Town | 2 - 0 |  Seaham Red Star | Ebac Northern League Division 1 | |
| 2021-08-20 18:15:0020/08/2021 | George & Dragon Vets 1 | 3 - 0 | Guisborough Town Over 35s | Celestial Windows Middlesbrough Over 35 League | |
| 2021-08-21 15:00:3321/08/2021 | North Shields | 2 - 0 | Guisborough Town | Emirates FA Cup | |
| 2021-08-25 19:45:0025/08/2021 | Guisborough Town | 3 - 0 |  West Allotment Celtic | Ebac Northern League Division 1 | |
| 2021-08-27 18:15:0027/08/2021 | Guisborough Town Over 35s | 0 - 9 | Whinney Banks Vets | Celestial Windows Middlesbrough Over 35 League | |
| 2021-08-28 15:00:0028/08/2021 | Guisborough Town | 0 - 0 | Newton Aycliffe | Ebac Northern League Division 1 | |
| 2021-08-30 11:00:0030/08/2021 | Northallerton Town | 2 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2021-09-04 13:30:4104/09/2021 | Guisborough Town U18 | 3 - 1 | Norton & Stockton Ancients | Friendly | |
| 2021-09-04 14:00:0004/09/2021 | Guisborough Town Reserves | 2 - 1 | Redcar Town Reserves | North Riding Division 1 East | |
| 2021-09-04 15:00:0004/09/2021 | Billingham Town | 0 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2021-09-05 14:00:0005/09/2021 | Brooklyn Ladies FC  | 6 - 1 | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2021-09-11 13:30:0611/09/2021 | Guisborough Town U18 | 13:30:0613:30 | Morpeth Town | U18's Saturday Afternoon League | |
| 2021-09-11 14:00:0011/09/2021 | Whitby Fishermens Society  | 2 - 3 | Guisborough Town Reserves | North Riding Division 1 East | |
| 2021-09-11 15:00:0211/09/2021 | Carlisle City  | 1 - 0 | Guisborough Town | Buildbase FA Vase | |
| 2021-09-12 14:00:0012/09/2021 | GTFC Ladies Reserves | P - P | Huntington Rovers Ladies | North Riding Womens Premier League | |
| 2021-09-12 14:00:5812/09/2021 | Guisborough Town Ladies | 0 - 12 |  Gateshead FC Ladies | Adobe Women's FA Cup | |
| 2021-09-18 13:30:2618/09/2021 | Billingham Town | H - W | Guisborough Town U18 | U18's Saturday Afternoon League | |
| 2021-09-18 14:00:0018/09/2021 | Guisborough Town Reserves | 0 - 3 |  Lealholm | North Riding Division 1 East | |
| 2021-09-18 15:00:0018/09/2021 | Guisborough Town | 0 - 4 | Thornaby | Ebac Northern League Division 1 | |
| 2021-09-19 14:00:0019/09/2021 | Spennymoor Town Youth Ladies  | 8 - 1 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2021-09-19 14:00:0019/09/2021 | Redcar Athletic Ladies | 16 - 0 | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2021-09-25 13:30:2225/09/2021 | Guisborough Town U18 | 13:30:2213:30 | | U18's Saturday Afternoon League | |
| 2021-09-25 14:00:0025/09/2021 | New Marske FC  | 0 - 3 | Guisborough Town Reserves | North Riding Division 1 East | |
| 2021-09-25 15:00:0025/09/2021 | Crook Town  | 1 - 3 | Guisborough Town | Ebac Northern League Division 1 | |
| 2021-09-26 14:00:0026/09/2021 | Guisborough Town Ladies | C - C |  Chester le Street Town Ladies Development | North East Regional Womens Football League Northern | |
| 2021-09-26 14:00:0026/09/2021 | GTFC Ladies Reserves | 4 - 3 | Brompton Ladies | North Riding Womens Premier League | |
| 2021-10-02 13:30:2202/10/2021 | Durham United FC  | 13:30:2213:30 | Guisborough Town U18 | U18's Saturday Afternoon League | |
| 2021-10-02 14:00:2502/10/2021 | Edgehill FC Reserves | A - W | Guisborough Town Reserves | North Riding Division 1 East | |
| 2021-10-02 15:00:0002/10/2021 | Consett | 3 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2021-10-03 14:00:0003/10/2021 | Thornaby FC Ladies | 26 - 0 | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2021-10-09 13:30:1909/10/2021 | Guisborough Town U18 | 13:30:1913:30 | Bishop Auckland | U18's Saturday Afternoon League | |
| 2021-10-09 14:00:4009/10/2021 | Boro Rangers U21  | 2 - 0 | Guisborough Town Reserves | North Riding Division 1 East | |
| 2021-10-09 15:00:0009/10/2021 | Guisborough Town | 0 - 1 | West Auckland Town | Ebac Northern League Division 1 | |
| 2021-10-10 14:00:0010/10/2021 | Guisborough Town Ladies | 1 - 9 | Bishop Auckland Ladies First | North East Regional Womens Football League Northern | |
| 2021-10-10 14:00:0010/10/2021 | GTFC Ladies Reserves | 6 - 5 | Scarborough Athletic Ladies | North Riding Womens Premier League | |
| 2021-10-16 14:00:5716/10/2021 | Guisborough Town Reserves | 7 - 1 |  Loftus Athletic | North Riding Division 1 East | |
| 2021-10-16 15:00:0016/10/2021 | Sunderland Ryhope C.W. | 1 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2021-10-17 14:00:0017/10/2021 | Blyth Town Ladies | H - W | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2021-10-17 14:00:0017/10/2021 | Poppleton Ladies | 11 - 1 | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2021-10-20 19:30:0020/10/2021 | Newcastle Benfield | 0 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2021-10-23 14:00:1423/10/2021 | Redcar Town Reserves | 14:00:1414:00 | | North Riding Division 1 East | |
| 2021-10-23 14:00:4023/10/2021 | Loftus Athletic | 2 - 1 | Guisborough Town Reserves | North Riding Division 1 East | |
| 2021-10-23 15:00:0023/10/2021 | Whitley Bay | 2 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2021-10-24 14:00:0024/10/2021 | Guisborough Town Ladies | 1 - 5 | Boro Rangers Women | North East Regional Womens Football League Northern | |
| 2021-10-24 14:00:0024/10/2021 | GTFC Ladies Reserves | 0 - 6 | Redcar Town Ladies Reserves | North Riding Womens Premier League | |
| 2021-10-30 15:00:0030/10/2021 | Guisborough Town | 0 - 4 | North Shields | Ebac Northern League Division 1 | |
| 2021-10-31 14:00:0031/10/2021 | Wallsend B.C. Womens Reserves  | 9 - 1 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2021-11-06 14:00:4406/11/2021 | Lealholm | 1 - 2 | Guisborough Town Reserves | WOODSmith Construction North Riding Saturday Challenge Cup | |
| 2021-11-06 15:00:0006/11/2021 | Redcar Athletic | 0 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2021-11-07 14:00:0007/11/2021 | Guisborough Town Ladies | 0 - 13 |  Chester le Street United Women First | North East Regional Womens Football League Northern | |
| 2021-11-07 14:00:0007/11/2021 | GTFC Ladies Reserves | 3 - 2 |  Acklam Ladies | North Riding Womens Premier League | |
| 2021-11-13 14:00:5413/11/2021 | Boro Rangers U21 | 1 - 1 | Guisborough Town Reserves | North Riding Division 1 East | |
| 2021-11-13 15:00:0013/11/2021 | Guisborough Town | 1 - 2 | Penrith | Ebac Northern League Division 1 | |
| 2021-11-14 14:00:0014/11/2021 | West Allotment Celtic Ladies | 5 - 2 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2021-11-14 14:00:0014/11/2021 | Richmond Town Women | 10 - 0 | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2021-11-20 15:00:0020/11/2021 | Sunderland RCA | 1 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2021-11-21 14:00:0021/11/2021 | Norton & Stockton Ancients LFC Reserves  | 6 - 2 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2021-11-24 19:45:0824/11/2021 | Guisborough Town | 1 - 1 | Middlesbrough FC U23 | WOODSmith Construction North Riding Senior Cup | |
| 2021-12-04 15:00:0004/12/2021 | Guisborough Town | 2 - 2 | Northallerton Town | Ebac Northern League Division 1 | |
| 2021-12-04 15:00:1804/12/2021 | New Marske FC | 4 - 2 | Guisborough Town Reserves | WOODSmith Construction North Riding Saturday Challenge Cup | |
| 2021-12-11 15:00:0011/12/2021 | West Allotment Celtic | 3 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2021-12-18 14:00:0818/12/2021 | Guisborough Town Reserves | 2 - 2 |  Great Ayton United | North Riding Division 1 East | |
| 2021-12-18 15:00:0018/12/2021 | Guisborough Town | 3 - 2 | Whickham | Ebac Northern League Division 1 | |
| 2021-12-19 14:00:1819/12/2021 | GTFC Ladies Reserves | 8 - 4 | Brooklyn Ladies FC | North Riding Womens Premier League | |
| 2022-01-08 14:00:3908/01/2022 | Guisborough Town Reserves | 6 - 0 | Redcar Town Reserves | North Riding Division 1 East | |
| 2022-01-12 19:45:4612/01/2022 | Guisborough Town | P - P | Crook Town | Brooks Mileson Memorial Northern League Cup | |
| 2022-01-15 14:00:2215/01/2022 | Guisborough Town U18 | 14:00:2214:00 | | North Riding U19 County Cup | |
| 2022-01-15 14:00:5115/01/2022 | Guisborough Town Reserves | 3 - 2 |  South Park Rangers | North Riding Division 1 East | |
| 2022-01-15 15:00:0015/01/2022 | Guisborough Town | 4 - 1 | Newcastle Benfield | Ebac Northern League Division 1 | |
| 2022-01-16 14:00:3416/01/2022 | Guisborough Town Ladies | 15 - 1 | | North Riding Womens Cup | |
| 2022-01-16 14:00:5016/01/2022 | GTFC Ladies Reserves | 0 - 4 | Redcar Athletic Ladies | North Riding Womens Cup | |
| 2022-01-22 14:00:1022/01/2022 | Guisborough Town Reserves | 1 - 4 | Boro Rangers U21 | North Riding Division 1 East | |
| 2022-01-22 15:00:0022/01/2022 | Guisborough Town | 4 - 3 | Redcar Athletic | Ebac Northern League Division 1 | |
| 2022-01-23 14:00:2023/01/2022 | Huntington Rovers Ladies | 11 - 0 | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2022-01-23 14:00:3623/01/2022 | Bishop Auckland Ladies First | 5 - 1 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2022-01-25 19:45:2425/01/2022 | Pickering Town  | 3 - 4 | Guisborough Town | WOODSmith Construction North Riding Senior Cup | |
| 2022-01-29 14:00:0729/01/2022 | Guisborough Town Reserves | 5 - 1 | Whitby Fishermens Society | North Riding Division 1 East | |
| 2022-01-29 15:00:0029/01/2022 | Guisborough Town | 1 - 1 | Crook Town | Ebac Northern League Division 1 | |
| 2022-01-30 14:00:2030/01/2022 | GTFC Ladies Reserves | 2 - 2 | Poppleton Ladies | North Riding Womens Premier League | |
| 2022-01-30 14:00:5330/01/2022 | Guisborough Town Ladies | 1 - 9 | Blyth Town Ladies | North East Regional Womens Football League Northern | |
| 2022-02-05 14:00:1205/02/2022 | Lealholm | 0 - 1 | Guisborough Town Reserves | North Riding Division 1 East | |
| 2022-02-05 15:00:0005/02/2022 | Newton Aycliffe | 1 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-02-06 14:00:2706/02/2022 | GTFC Ladies Reserves | 0 - 11 | Redcar Athletic Ladies | North Riding Womens Premier League | |
| 2022-02-06 14:00:5606/02/2022 | Boro Rangers Women | 3 - 0 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2022-02-12 14:00:5712/02/2022 | Guisborough Town Reserves | 0 - 2 | New Marske FC | North Riding Division 1 East | |
| 2022-02-12 15:00:0012/02/2022 | Guisborough Town | 2 - 0 | Billingham Town | Ebac Northern League Division 1 | |
| 2022-02-13 14:00:5813/02/2022 | Guisborough Town Ladies | 2 - 4 | Wallsend B.C. Womens Reserves | North East Regional Womens Football League Northern | |
| 2022-02-19 14:00:4819/02/2022 | Guisborough Town Reserves | 3 - 0 | | North Riding Division 1 East | |
| 2022-02-19 15:00:0019/02/2022 | Guisborough Town | 0 - 2 | Consett | Ebac Northern League Division 1 | |
| 2022-02-20 14:00:0420/02/2022 | Chester le Street United Women First | 13 - 0 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2022-02-26 14:00:3326/02/2022 | Great Ayton United | 0 - 0 | Guisborough Town Reserves | North Riding Division 1 East | |
| 2022-02-26 15:00:0026/02/2022 | Seaham Red Star | 1 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-02-27 14:15:0227/02/2022 | GTFC Ladies Reserves | 3 - 6 | Richmond Town Women | North Riding Womens Premier League | |
| 2022-03-05 14:00:2105/03/2022 | Guisborough Town Reserves | P - P | Loftus Athletic | North Riding Division 1 East | |
| 2022-03-05 15:00:0005/03/2022 | Penrith | 2 - 3 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-03-06 14:00:0406/03/2022 | Brompton Ladies | P - P | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2022-03-06 14:00:0606/03/2022 | Wallsend B.C. Womens Reserves | 5 - 1 | Guisborough Town Ladies | North Riding Womens Cup | |
| 2022-03-06 14:00:0906/03/2022 | Acklam Ladies | C - C | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2022-03-09 19:45:5309/03/2022 | Guisborough Town | 4 - 0 | Penrith | Northern League Division One Cup | |
| 2022-03-12 14:00:0712/03/2022 | Lealholm | 5 - 1 | Guisborough Town Reserves | North Riding Division 1 East | |
| 2022-03-12 15:00:0012/03/2022 | West Auckland Town | 1 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-03-13 14:00:0413/03/2022 | Washington AFC Womens | 2 - 1 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2022-03-13 14:00:2813/03/2022 | Redcar Town Ladies Reserves | 6 - 0 | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2022-03-19 14:00:2019/03/2022 | New Marske FC | 1 - 1 | Guisborough Town Reserves | North Riding Division 1 East | |
| 2022-03-19 15:00:0019/03/2022 | Ashington | 1 - 6 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-03-20 14:00:0020/03/2022 | Prudhoe Town Women First  | 0 - 1 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2022-03-26 14:00:3226/03/2022 | South Park Rangers | 4 - 0 | Guisborough Town Reserves | North Riding Division 1 East | |
| 2022-03-26 15:00:0026/03/2022 | Guisborough Town | 1 - 1 | Whitley Bay | Ebac Northern League Division 1 | |
| 2022-03-27 14:00:4527/03/2022 | Guisborough Town Ladies | 3 - 3 | West Allotment Celtic Ladies | North East Regional Womens Football League Northern | |
| 2022-03-30 19:45:0130/03/2022 | Guisborough Town | 1 - 0 | Marske United | WOODSmith Construction North Riding Senior Cup | |
| 2022-04-02 14:00:2202/04/2022 | Redcar Town Reserves | P - P | Guisborough Town Reserves | North Riding Division 1 East | |
| 2022-04-02 15:00:0002/04/2022 | North Shields | 4 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-04-03 14:00:0003/04/2022 | Guisborough Town Ladies | 2 - 4 | Norton & Stockton Ancients LFC Reserves | North East Regional Womens Football League Northern | |
| 2022-04-05 19:45:5405/04/2022 | Ashington | 3 - 1 | Guisborough Town | Northern League Division One Cup | |
| 2022-04-09 14:00:1309/04/2022 | Great Ayton United | 0 - 0 | Guisborough Town Reserves | North Riding Division 1 East | |
| 2022-04-09 15:00:0009/04/2022 | Whickham | 3 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-04-10 14:00:0010/04/2022 | Guisborough Town Ladies | 2 - 2 | Spennymoor Town Youth Ladies | North East Regional Womens Football League Northern | |
| 2022-04-10 14:00:4610/04/2022 | GTFC Ladies Reserves | 0 - 13 | Thornaby FC Ladies | North Riding Womens Premier League | |
| 2022-04-16 15:00:0016/04/2022 | Guisborough Town | 1 - 1 | Sunderland Ryhope C.W. | Ebac Northern League Division 1 | |
| 2022-04-19 19:45:0019/04/2022 | Bishop Auckland | 0 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-04-23 15:00:0023/04/2022 | Thornaby | 1 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-05-01 14:00:0601/05/2022 | Guisborough Town Ladies | 0 - 1 | Washington AFC Womens | North East Regional Womens Football League Northern | |
| 2022-05-01 14:00:4101/05/2022 | GTFC Ladies Reserves | 1 - 2 | Poppleton Ladies | North Riding Womens Premier League | |
| 2022-05-04 19:30:2704/05/2022 | Guisborough Town | 0 - 3 |  Scarborough Athletic | WOODSmith Construction North Riding Senior Cup | |
| 2022-05-08 14:00:1508/05/2022 | Guisborough Town Ladies | 4 - 1 | Prudhoe Town Women First | North East Regional Womens Football League Northern | |
| 2022-07-02 15:00:3702/07/2022 | Grangetown Boys Club  | 0 - 5 | Guisborough Town | Friendly | |
| 2022-07-06 19:45:0806/07/2022 | Guisborough Town | 1 - 3 | Middlesbrough FC U23 | Friendly | |
| 2022-07-09 15:00:4009/07/2022 | Guisborough Town | 1 - 2 | Marske United | John Butterfield Memorial Trophy | |
| 2022-07-13 19:45:5813/07/2022 | Thornaby | 1 - 2 | Guisborough Town | Peter Morris Memorial Trophy | |
| 2022-07-16 12:00:0116/07/2022 | Redcar Athletic | 0 - 1 | Guisborough Town | Mo Mowlam Memorial Cup | |
| 2022-07-17 15:00:4717/07/2022 | Guisborough Town | 2 - 5 | Marske United | Mo Mowlam Memorial Cup | |
| 2022-07-20 19:45:2820/07/2022 | Stockton Town | C - C | Guisborough Town | Friendly | |
| 2022-07-26 19:45:4726/07/2022 | Whitby Town | 3 - 0 | Guisborough Town | Micky Skinner Memorial Trophy | |
| 2022-07-30 15:00:0030/07/2022 | Thornaby | 2 - 3 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-08-02 19:45:0002/08/2022 | West Auckland Town | 1 - 4 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-08-06 15:00:0606/08/2022 | Guisborough Town | 0 - 1 | Bishop Auckland | Emirates FA Cup | |
| 2022-08-10 19:45:0010/08/2022 | Guisborough Town | 1 - 1 | Newcastle Benfield | Ebac Northern League Division 1 | |
| 2022-08-16 19:30:0016/08/2022 | Whickham | 0 - 3 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-08-20 15:00:0020/08/2022 | Guisborough Town | 2 - 1 | Penrith | Ebac Northern League Division 1 | |
| 2022-08-24 19:45:0024/08/2022 | Guisborough Town | 3 - 3 |  Tow Law Town | Ebac Northern League Division 1 | |
| 2022-08-27 15:00:2127/08/2022 | Guisborough Town | 6 - 1 | Washington | Isuzu FA Vase | |
| 2022-09-02 19:45:0002/09/2022 | Guisborough Town | 1 - 2 | Seaham Red Star | Ebac Northern League Division 1 | |
| 2022-09-04 14:00:0004/09/2022 | GTFC Ladies Reserves | 2 - 2 | Boro Rangers | North Riding Womens Premier League | |
| 2022-09-04 14:00:0004/09/2022 | Guisborough Town Ladies | 0 - 8 | Wallsend B.C. Womens Reserves | North East Regional Womens Football League Northern | |
| 2022-09-17 15:00:0017/09/2022 | Carlisle City | 0 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-09-18 14:00:0018/09/2022 | Richmond Town Women | 12 - 0 | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2022-09-18 14:00:0518/09/2022 | Guisborough Town Ladies | 1 - 5 | West Allotment Celtic Ladies | Adobe Women's FA Cup | |
| 2022-09-20 19:30:0020/09/2022 | Newton Aycliffe | 3 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-09-24 15:00:2024/09/2022 | Kendal Town  | 3 - 1 | Guisborough Town | Isuzu FA Vase | |
| 2022-09-25 14:00:0025/09/2022 | GTFC Ladies Reserves | 1 - 8 | Richmond Town Women | North Riding Womens Premier League | |
| 2022-09-25 14:00:0025/09/2022 | Guisborough Town Ladies | 2 - 2 | Bishop Auckland Ladies First | North East Regional Womens Football League Northern | |
| 2022-10-01 15:00:0001/10/2022 | Penrith | 0 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-10-02 14:00:0002/10/2022 | York City Ladies Development  | 13 - 0 | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2022-10-02 14:00:0002/10/2022 | Chester le Street United Women First | 7 - 0 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2022-10-05 19:45:0005/10/2022 | Guisborough Town | 2 - 4 | Bishop Auckland | Ebac Northern League Division 1 | |
| 2022-10-08 15:00:0008/10/2022 | Seaham Red Star | 1 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-10-09 14:00:0009/10/2022 | GTFC Ladies Reserves | 0 - 7 |  Middlesbrough Development | North Riding Womens Premier League | |
| 2022-10-09 14:00:0009/10/2022 | Guisborough Town Ladies | 1 - 5 | Gateshead FC Ladies | North East Regional Womens Football League Northern | |
| 2022-10-12 19:30:0012/10/2022 | Crook Town | 2 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-10-15 15:00:0015/10/2022 | Redcar Athletic | 3 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-10-16 14:00:0016/10/2022 | Kader  | 1 - 3 | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2022-10-22 15:00:0022/10/2022 | Guisborough Town | 4 - 0 | Crook Town | Ebac Northern League Division 1 | |
| 2022-10-23 14:00:0023/10/2022 | GTFC Ladies Reserves | 2 - 11 | Redcar Athletic | North Riding Womens Premier League | |
| 2022-10-23 14:00:0023/10/2022 | Hartlepool Pools Youth Ladies  | 6 - 1 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2022-10-29 15:00:0029/10/2022 | Pickering Town | 0 - 3 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-10-30 14:00:0030/10/2022 | Huntington Rovers Ladies | 2 - 0 | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2022-10-30 14:00:0030/10/2022 | Guisborough Town Ladies | 0 - 5 |  Hartlepool United Women FC First | North East Regional Womens Football League Northern | |
| 2022-11-05 15:00:0005/11/2022 | Guisborough Town | 2 - 1 | Sunderland RCA | Ebac Northern League Division 1 | |
| 2022-11-06 14:00:0006/11/2022 | GTFC Ladies Reserves | 0 - 9 | Northallerton Town | North Riding Womens Premier League | |
| 2022-11-06 14:00:0006/11/2022 | Norton & Stockton Ancients LFC Reserves | 6 - 0 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2022-11-12 15:00:0012/11/2022 | Guisborough Town | 2 - 1 | West Auckland Town | Ebac Northern League Division 1 | |
| 2022-11-13 14:00:0013/11/2022 | GTFC Ladies Reserves | 2 - 7 | York St. John University Women’s | North Riding Womens Premier League | |
| 2022-11-13 14:00:0013/11/2022 | Guisborough Town Ladies | 1 - 4 | Spennymoor Town Youth Ladies | North East Regional Womens Football League Northern | |
| 2022-11-20 14:00:4420/11/2022 | North Ormesby  | 0 - 12 | Guisborough Town U18 | North Riding U19 County Cup | |
| 2022-11-23 19:45:4923/11/2022 | Guisborough Town | 5 - 1 | Richmond Town | WOODSmith Construction North Riding Senior Cup | |
| 2022-11-26 15:00:0026/11/2022 | Guisborough Town | 2 - 1 | Whickham | Ebac Northern League Division 1 | |
| 2022-11-27 14:00:0027/11/2022 | Guisborough Town Ladies | 1 - 7 | Thornaby FC Ladies | North East Regional Womens Football League Northern | |
| 2022-12-04 14:00:0004/12/2022 | Wallsend B.C. Womens Reserves | 3 - 1 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2022-12-11 14:00:0011/12/2022 | Guisborough Town Ladies | 0 - 3 | Washington AFC Womens | North East Regional Womens Football League Northern | |
| 2022-12-26 11:00:0026/12/2022 | Guisborough Town | 2 - 2 | Northallerton Town | Ebac Northern League Division 1 | |
| 2023-01-07 15:00:0007/01/2023 | Heaton Stannington  | 2 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-01-08 14:00:0008/01/2023 | Middlesbrough Development | 5 - 0 | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2023-01-08 14:00:0008/01/2023 | Bishop Auckland Ladies First | 5 - 0 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2023-01-11 19:45:0011/01/2023 | Guisborough Town | 2 - 3 | Newton Aycliffe | Ebac Northern League Division 1 | |
| 2023-01-14 15:00:0014/01/2023 | Guisborough Town | 2 - 0 | Thornaby | Ebac Northern League Division 1 | |
| 2023-01-15 14:00:3115/01/2023 | York City Ladies | H - W | GTFC Ladies Reserves | North Riding Womens Cup | |
| 2023-01-15 14:00:5215/01/2023 | Redcar Town | 11 - 0 | Guisborough Town Ladies | North Riding Womens Cup | |
| 2023-01-22 14:00:0022/01/2023 | Gateshead FC Ladies | 7 - 0 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2023-01-24 19:30:4624/01/2023 | Redcar Town | 1 - 5 | Guisborough Town | WOODSmith Construction North Riding Senior Cup | |
| 2023-01-28 15:00:0028/01/2023 | Newcastle Benfield | 1 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-01-29 14:00:0029/01/2023 | GTFC Ladies Reserves | 1 - 2 | Huntington Rovers Ladies | North Riding Womens Premier League | |
| 2023-01-29 14:00:0029/01/2023 | Guisborough Town Ladies | 0 - 3 | West Allotment Celtic Ladies | North East Regional Womens Football League Northern | |
| 2023-02-04 15:00:0004/02/2023 | West Allotment Celtic | 0 - 5 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-02-05 14:00:0005/02/2023 | GTFC Ladies Reserves | 9 - 1 |  Old Malton St. Marys | North Riding Womens Premier League | |
| 2023-02-05 14:00:0005/02/2023 | Guisborough Town Ladies | 0 - 3 | Hartlepool Pools Youth Ladies | North East Regional Womens Football League Northern | |
| 2023-02-07 19:45:0007/02/2023 | Bishop Auckland | 2 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-02-11 15:00:0011/02/2023 | Guisborough Town | 0 - 1 | Ashington | Ebac Northern League Division 1 | |
| 2023-02-12 14:00:0012/02/2023 | Hartlepool United Women FC First | 5 - 0 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2023-02-18 15:00:0018/02/2023 | Whitley Bay | 1 - 3 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-02-19 14:00:0019/02/2023 | Old Malton St. Marys | 4 - 0 | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2023-02-19 14:00:1319/02/2023 | Washington AFC Womens | 14:00:1314:00 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2023-02-24 19:30:0024/02/2023 | Spennymoor Town Youth Ladies | 8 - 0 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2023-02-25 15:00:0025/02/2023 | Guisborough Town | 3 - 3 | Carlisle City | Ebac Northern League Division 1 | |
| 2023-02-26 14:00:0026/02/2023 | GTFC Ladies Reserves | 0 - 3 | Poppleton Ladies | North Riding Womens Premier League | |
| 2023-03-05 14:00:0005/03/2023 | Poppleton Ladies | 7 - 0 | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2023-03-05 14:00:0005/03/2023 | Guisborough Town Ladies | 0 - 1 | Chester le Street United Women First | North East Regional Womens Football League Northern | |
| 2023-03-08 19:30:2808/03/2023 | Guisborough Town | 1 - 2 | South Park Rangers | WOODSmith Construction North Riding Senior Cup | |
| 2023-03-11 15:00:0011/03/2023 | Ashington | 1 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-03-18 15:00:0018/03/2023 | Guisborough Town | 0 - 0 | Whitley Bay | Ebac Northern League Division 1 | |
| 2023-03-22 19:45:0022/03/2023 | Guisborough Town | 4 - 2 | Pickering Town | Ebac Northern League Division 1 | |
| 2023-03-25 15:00:0025/03/2023 | Guisborough Town | 0 - 1 | Redcar Athletic | Ebac Northern League Division 1 | |
| 2023-03-26 14:00:0026/03/2023 | GTFC Ladies Reserves | 0 - 13 | York City Ladies Development | North Riding Womens Premier League | |
| 2023-03-26 14:00:0026/03/2023 | Guisborough Town Ladies | 0 - 7 | Norton & Stockton Ancients LFC Reserves | North East Regional Womens Football League Northern | |
| 2023-04-01 15:00:0001/04/2023 | Guisborough Town | 2 - 2 | Heaton Stannington | Ebac Northern League Division 1 | |
| 2023-04-02 14:00:0002/04/2023 | Redcar Athletic | 10 - 0 | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2023-04-07 15:00:0007/04/2023 | Northallerton Town | 2 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-04-13 19:30:0013/04/2023 | Tow Law Town | 3 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-04-15 15:00:0015/04/2023 | Guisborough Town | 0 - 2 | West Allotment Celtic | Ebac Northern League Division 1 | |
| 2023-04-16 14:00:0016/04/2023 | Northallerton Town | 8 - 0 | GTFC Ladies Reserves | North Riding Womens Premier League | |
| 2023-04-16 14:00:0016/04/2023 | Thornaby FC Ladies | 1 - 1 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2023-04-22 15:00:0022/04/2023 | Sunderland RCA | 0 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-04-23 14:00:0023/04/2023 | GTFC Ladies Reserves | 3 - 0 | Kader | North Riding Womens Premier League | |
| 2023-05-07 14:00:0007/05/2023 | West Allotment Celtic Ladies | 4 - 4 | Guisborough Town Ladies | North East Regional Womens Football League Northern | |
| 2023-07-01 13:30:2801/07/2023 | Yarm & Eaglescliffe FC  | 2 - 2 | Guisborough Town | Friendly | |
| 2023-07-07 19:45:5407/07/2023 | Kader | 1 - 7 | Guisborough Town | Friendly | |
| 2023-07-11 19:45:3911/07/2023 | Guisborough Town | 1 - 1 | Marske United | John Butterfield Memorial Trophy | |
| 2023-07-15 13:00:0015/07/2023 | Thornaby | 2 - 0 | Guisborough Town | Peter Morris Memorial Trophy | |
| 2023-07-19 19:45:2919/07/2023 | Richmond Town | 1 - 5 | Guisborough Town | Friendly | |
| 2023-07-22 13:00:4822/07/2023 | Stockton Town | 0 - 1 | Guisborough Town | Friendly | |
| 2023-07-25 15:00:5925/07/2023 | Guisborough Town | P - P | Whitby Town | Friendly | |
| 2023-07-29 15:00:0029/07/2023 | West Auckland Town | 2 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-08-01 19:30:0001/08/2023 | Birtley Town  | 2 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-08-09 19:45:2209/08/2023 | Guisborough Town | 2 - 2 | Newton Aycliffe | Emirates FA Cup | |
| 2023-08-12 14:00:0912/08/2023 | Guisborough Town Reserves | 0 - 1 | Yarm & Eaglescliffe FC Reserves | North Riding Division 1 | |
| 2023-08-12 15:00:0012/08/2023 | West Allotment Celtic | 1 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-08-15 19:30:4815/08/2023 | Newton Aycliffe | 2 - 3 | Guisborough Town | Emirates FA Cup | |
| 2023-08-16 19:00:4216/08/2023 | Guisborough Town Reserves | 3 - 2 |  Whinney Banks YCC | North Riding Division 1 | |
| 2023-08-19 14:00:5019/08/2023 | Heighington FC  | 3 - 0 | Guisborough Town Reserves | North Riding Division 1 | |
| 2023-08-19 15:00:1619/08/2023 | Pontefract Collieries  | 1 - 3 | Guisborough Town | Emirates FA Cup | |
| 2023-08-23 19:45:0023/08/2023 | Guisborough Town | 1 - 2 | Bishop Auckland | Ebac Northern League Division 1 | |
| 2023-08-26 14:00:1226/08/2023 | Guisborough Town Reserves | 1 - 2 | Redcar Town Reserves | North Riding Division 1 | |
| 2023-08-26 15:00:0026/08/2023 | North Shields | 1 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-08-30 19:30:2130/08/2023 | Guisborough Town Reserves | P - P | Marske United Reserves | North Riding Division 1 | |
| 2023-08-30 19:45:0030/08/2023 | Guisborough Town | 3 - 1 | Sunderland RCA | Ebac Northern League Division 1 | |
| 2023-08-30 19:45:1830/08/2023 | Marske United Reserves | 0 - 4 | Guisborough Town Reserves | North Riding Division 1 | |
| 2023-09-02 14:00:1702/09/2023 | Whinney Banks YCC | 2 - 6 | Guisborough Town Reserves | WOODSmith Construction North Riding Saturday Challenge Cup | |
| 2023-09-02 15:00:4802/09/2023 | Guisborough Town | 0 - 4 |  Atherton Collieries | Emirates FA Cup | |
| 2023-09-03 14:00:0003/09/2023 | Guisborough Town Ladies | 6 - 0 | Redcar Athletic Ladies | North Riding Womens Premier League | |
| 2023-09-06 19:45:0006/09/2023 | Guisborough Town | 2 - 2 | Redcar Athletic | Ebac Northern League Division 1 | |
| 2023-09-08 19:30:1108/09/2023 | Thirsk Falcons Development  | 0 - 2 | Guisborough Town Reserves | North Riding Division 1 | |
| 2023-09-09 15:00:0009/09/2023 | Guisborough Town | 2 - 1 | Penrith | Ebac Northern League Division 1 | |
| 2023-09-10 14:00:1110/09/2023 | Guisborough Town Ladies | 5 - 2 | Chester le Street United Women First | Adobe Women's FA Cup | |
| 2023-09-13 19:30:0213/09/2023 | Guisborough Town Reserves | 5 - 1 | Loftus Athletic | North Riding Division 1 | |
| 2023-09-16 14:00:3016/09/2023 | Guisborough Town Reserves | 5 - 0 |  Billingham Town Development | North Riding Division 1 | |
| 2023-09-17 14:00:0017/09/2023 | Guisborough Town Ladies | 14 - 0 |  Skelton United Ladies | North Riding Womens Premier League | |
| 2023-09-22 19:45:0922/09/2023 | Guisborough Town | 5 - 1 | Redcar Town | Isuzu FA Vase | |
| 2023-09-23 14:00:0223/09/2023 | Boro Rangers U21 | 0 - 2 | Guisborough Town Reserves | North Riding Division 1 | |
| 2023-09-24 14:00:0024/09/2023 | Huntington Rovers Ladies | 0 - 8 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2023-09-27 19:30:5627/09/2023 | Redcar Town Reserves | 0 - 0 | Guisborough Town Reserves | North Riding Division 1 | |
| 2023-09-30 14:00:5130/09/2023 | Guisborough Town Reserves | 1 - 1 | Richmond Town Reserves | North Riding Division 1 | |
| 2023-09-30 15:00:0030/09/2023 | Guisborough Town | 2 - 1 | Whickham | Ebac Northern League Division 1 | |
| 2023-10-01 14:00:5101/10/2023 | Guisborough Town Ladies | 4 - 0 |  Horden CW Women | Adobe Women's FA Cup | |
| 2023-10-07 14:00:2207/10/2023 | Loftus Athletic | 2 - 4 | Guisborough Town Reserves | WOODSmith Construction North Riding Saturday Challenge Cup | |
| 2023-10-08 14:00:0008/10/2023 | T.I.B.S Women  | 0 - 14 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2023-10-14 14:00:3314/10/2023 | Tees FC  | 0 - 10 | Guisborough Town Reserves | North Riding Division 1 | |
| 2023-10-14 15:00:0014/10/2023 | Guisborough Town | 2 - 0 | Whitley Bay | Ebac Northern League Division 1 | |
| 2023-10-15 14:00:0015/10/2023 | Northallerton Town Women  | 1 - 9 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2023-10-21 15:00:5021/10/2023 | Emley AFC  | 2 - 1 | Guisborough Town | Isuzu FA Vase | |
| 2023-10-22 14:00:3422/10/2023 | Guisborough Town Ladies | 1 - 6 |  Stockport County | Adobe Women's FA Cup | |
| 2023-10-28 14:00:1428/10/2023 | Tees FC | 0 - 9 | Guisborough Town Reserves | Macmillan Bowl | |
| 2023-10-28 15:00:0028/10/2023 | Guisborough Town | 2 - 2 | Newcastle Benfield | Ebac Northern League Division 1 | |
| 2023-10-29 14:00:0029/10/2023 | York City Ladies U23 | 1 - 2 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2023-11-01 19:45:2501/11/2023 | Guisborough Town | 3 - 2 |  York City | WOODSmith Construction North Riding Senior Cup | |
| 2023-11-04 15:00:0004/11/2023 | Shildon  | 1 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-11-11 14:00:1311/11/2023 | Guisborough Town Reserves | 3 - 0 |  Rawcliffe FC Reserves | WOODSmith Construction North Riding Saturday Challenge Cup | |
| 2023-11-11 15:00:0011/11/2023 | Guisborough Town | 0 - 1 | Crook Town | Ebac Northern League Division 1 | |
| 2023-11-12 14:00:0012/11/2023 | Richmond Town Women | 2 - 3 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2023-11-25 15:00:0025/11/2023 | Guisborough Town | 1 - 2 | Boro Rangers | Ebac Northern League Division 1 | |
| 2023-11-26 14:00:2426/11/2023 | Catterick Village Roses Ladies  | 2 - 10 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2023-12-08 14:00:0008/12/2023 | Yarm & Eaglescliffe FC Reserves | 5 - 0 | Guisborough Town Reserves | North Riding Division 1 | |
| 2023-12-09 15:00:0009/12/2023 | Guisborough Town | 3 - 4 | Birtley Town | Ebac Northern League Division 1 | |
| 2023-12-15 19:30:0015/12/2023 | Redcar Athletic | 1 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-12-16 14:00:4616/12/2023 | Guisborough Town Reserves | 2 - 1 | Kader | North Riding Division 1 | |
| 2023-12-19 19:30:0419/12/2023 | Guisborough Town | C - C | Crook Town | Brooks Mileson Memorial Northern League Cup | |
| 2023-12-22 19:30:0022/12/2023 | Boro Rangers | 2 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-12-26 12:00:0026/12/2023 | Guisborough Town | 3 - 0 | Northallerton Town | Ebac Northern League Division 1 | |
| 2023-12-30 15:00:0030/12/2023 | Guisborough Town | 3 - 0 | West Auckland Town | Ebac Northern League Division 1 | |
| 2024-01-06 15:00:0006/01/2024 | Bishop Auckland | 2 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-01-07 14:00:5907/01/2024 | Catterick Village Roses Ladies | 0 - 8 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2024-01-13 14:00:5213/01/2024 | Darlington R.A. | 6 - 2 | Guisborough Town Reserves | North Riding Division 1 | |
| 2024-01-13 15:00:0013/01/2024 | Guisborough Town | 1 - 0 | West Allotment Celtic | Ebac Northern League Division 1 | |
| 2024-01-14 14:00:4614/01/2024 | York Railway Institute Ladies Reserves | 2 - 0 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2024-01-20 14:00:0920/01/2024 | Kader | 1 - 2 | Guisborough Town Reserves | North Riding Division 1 | |
| 2024-01-21 14:00:4921/01/2024 | Redcar Athletic Ladies | 1 - 5 | Guisborough Town Ladies | North Riding Womens Cup | |
| 2024-01-27 14:00:3627/01/2024 | Guisborough Town Reserves | 3 - 2 |  Linthorpe Academicals FC | North Riding Division 1 | |
| 2024-01-27 15:00:0027/01/2024 | Guisborough Town | 2 - 0 | North Shields | Ebac Northern League Division 1 | |
| 2024-01-28 14:00:0028/01/2024 | South Park Rangers Belles | 2 - 7 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2024-02-03 15:00:0003/02/2024 | Penrith | 0 - 3 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-02-04 14:00:2404/02/2024 | Guisborough Town Ladies | 7 - 0 | Huntington Rovers Ladies | North Riding Womens Premier League | |
| 2024-02-10 14:00:0910/02/2024 | Guisborough Town Reserves | 4 - 1 | Bishopthorpe White Rose FC Firsts | WOODSmith Construction North Riding Saturday Challenge Cup | |
| 2024-02-13 19:45:2213/02/2024 | Guisborough Town | 1 (3) - 1 (2) | Scarborough Athletic | WOODSmith Construction North Riding Senior Cup | |
| 2024-02-17 14:00:2117/02/2024 | Guisborough Town Reserves | 12 - 0 | Tees FC | North Riding Division 1 | |
| 2024-02-17 15:00:0017/02/2024 | Whickham | 0 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-02-18 14:00:3418/02/2024 | Guisborough Town Ladies | 0 - 1 | York City Ladies Development | North Riding Womens Cup | |
| 2024-02-24 14:00:4924/02/2024 | Billingham Town Development | 0 - 6 | Guisborough Town Reserves | North Riding Division 1 | |
| 2024-02-24 15:00:0024/02/2024 | Guisborough Town | 2 - 1 | Carlisle City | Ebac Northern League Division 1 | |
| 2024-02-25 14:00:4125/02/2024 | Skelton United Ladies | 3 - 4 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2024-02-27 19:30:0027/02/2024 | Sunderland RCA | 0 - 6 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-03-02 14:00:1402/03/2024 | Carperby Rovers  | 2 - 1 | Guisborough Town Reserves | WOODSmith Construction North Riding Saturday Challenge Cup | |
| 2024-03-02 15:00:0002/03/2024 | Seaham Red Star | 0 - 3 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-03-03 14:00:0003/03/2024 | Guisborough Town Ladies | 4 - 0 | Old Malton St. Mary’s Ladies | North Riding Womens Premier League | |
| 2024-03-05 19:30:0005/03/2024 | Tow Law Town | 0 - 3 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-03-09 14:00:0709/03/2024 | Guisborough Town Reserves | 2 - 4 | Grangetown Boys Club | Macmillan Bowl | |
| 2024-03-09 15:00:0009/03/2024 | Whitley Bay | 2 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-03-12 19:45:0112/03/2024 | Guisborough Town | 1 (2) - 1 (4) | Whitby Town | WOODSmith Construction North Riding Senior Cup | |
| 2024-03-16 14:00:0316/03/2024 | Guisborough Town Reserves | 1 - 2 | Darlington R.A. | North Riding Division 1 | |
| 2024-03-16 15:00:0016/03/2024 | Guisborough Town | 1 - 1 | Seaham Red Star | Ebac Northern League Division 1 | |
| 2024-03-17 14:00:0017/03/2024 | Guisborough Town Ladies | 2 - 0 | Poppleton Ladies | North Riding Womens Premier League | |
| 2024-03-20 19:30:0020/03/2024 | Heaton Stannington | 3 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-03-23 14:00:4023/03/2024 | Guisborough Town Reserves | 1 - 2 | North Ormesby | North Riding Division 1 | |
| 2024-03-23 15:00:0023/03/2024 | Newcastle Benfield | 1 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-03-24 14:00:4324/03/2024 | Guisborough Town Ladies | 1 - 2 | Richmond Town Women | North Riding Womens Premier League | |
| 2024-03-27 19:30:1827/03/2024 | Guisborough Town Reserves | 5 - 1 | Marske United Reserves | North Riding Division 1 | |
| 2024-03-29 15:00:0029/03/2024 | Carlisle City | 2 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-03-30 14:00:4230/03/2024 | Linthorpe Academicals FC | 3 - 3 | Guisborough Town Reserves | North Riding Division 1 | |
| 2024-04-06 14:00:4006/04/2024 | North Ormesby | 2 - 3 | Guisborough Town Reserves | North Riding Division 1 | |
| 2024-04-06 15:00:0006/04/2024 | Guisborough Town | 2 - 1 | Shildon | Ebac Northern League Division 1 | |
| 2024-04-07 14:00:1607/04/2024 | Redcar Town Ladies Development | 0 - 5 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2024-04-10 19:45:0010/04/2024 | Guisborough Town | 4 - 0 | Tow Law Town | Ebac Northern League Division 1 | |
| 2024-04-11 18:00:2711/04/2024 | Guisborough Town Ladies | 6 - 0 | South Park Rangers Belles | North Riding Womens Premier League | |
| 2024-04-13 14:00:0013/04/2024 | Whinney Banks YCC | 2 - 4 | Guisborough Town Reserves | North Riding Division 1 | |
| 2024-04-13 15:00:0013/04/2024 | Crook Town | 1 - 3 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-04-14 14:00:5314/04/2024 | Guisborough Town Ladies | 5 - 0 | T.I.B.S Women | North Riding Womens Premier League | |
| 2024-04-17 18:30:0017/04/2024 | Redcar Town Ladies Development | 0 - 9 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2024-04-17 19:30:2917/04/2024 | Guisborough Town Reserves | 6 - 0 | Heighington FC | North Riding Division 1 | |
| 2024-04-20 14:00:4520/04/2024 | Richmond Town Reserves | 3 - 1 | Guisborough Town Reserves | North Riding Division 1 | |
| 2024-04-20 15:00:0020/04/2024 | Guisborough Town | 0 - 0 | Heaton Stannington | Ebac Northern League Division 1 | |
| 2024-04-21 14:00:0021/04/2024 | Guisborough Town Ladies | 2 - 2 | York Railway Institute Ladies Reserves | North Riding Womens Premier League | |
| 2024-04-24 19:15:3024/04/2024 | Guisborough Town Ladies | 6 - 1 | Northallerton Town Women | North Riding Womens Premier League | |
| 2024-04-24 19:30:0024/04/2024 | Northallerton Town | 0 - 3 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-04-27 14:00:0227/04/2024 | Loftus Athletic | 0 - 1 | Guisborough Town Reserves | North Riding Division 1 | |
| 2024-04-30 18:00:5730/04/2024 | Redcar Athletic Ladies | A - W | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2024-05-01 19:30:0901/05/2024 | Guisborough Town Reserves | 5 - 1 | Boro Rangers U21 | North Riding Division 1 | |
| 2024-05-02 18:00:1402/05/2024 | Old Malton St. Mary’s Ladies | 18:00:1418:00 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2024-05-03 19:30:5303/05/2024 | Guisborough Town Reserves | 3 - 1 | Thirsk Falcons Development | North Riding Division 1 | |
| 2024-05-05 14:00:1305/05/2024 | Poppleton Ladies | 2 - 11 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2024-05-11 15:00:5111/05/2024 | Guisborough Town Coaches Home | 3 - 5 | Guisborough Town Coaches Away | Fence Fundraiser | |
| 2024-05-12 14:00:2912/05/2024 | Guisborough Town Ladies | 0 - 8 | York City Ladies U23 | North Riding Womens Premier League | |
| 2024-07-06 14:00:4706/07/2024 | Thornaby | 0 - 2 | Guisborough Town | Peter Morris Memorial Trophy | |
| 2024-07-09 19:45:4209/07/2024 | Richmond Town | P - P | Guisborough Town | Friendly | |
| 2024-07-13 13:01:1713/07/2024 | Guisborough Town | C - C | Horden CW | Friendly | |
| 2024-07-16 19:30:3216/07/2024 | Yarm & Eaglescliffe FC | 0 - 1 | Guisborough Town | Friendly | |
| 2024-07-20 15:00:5820/07/2024 | Guisborough Town | 2(5) - 2(3) | Marske United | John Butterfield Memorial Trophy | |
| 2024-07-23 19:30:4723/07/2024 | Guisborough Town | 1 - 2 | Whitby Town | Micky Skinner Memorial Trophy | |
| 2024-07-27 15:00:0027/07/2024 | Northallerton Town | 1 - 3 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-07-30 19:45:0030/07/2024 | Kendal Town | 1 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-08-03 15:00:3603/08/2024 | Kendal Town | 2 - 2 | Guisborough Town | Emirates FA Cup | |
| 2024-08-07 19:45:5007/08/2024 | Guisborough Town | 1 - 2 | Kendal Town | Emirates FA Cup | |
| 2024-08-10 15:00:0010/08/2024 | Newcastle Blue Star  | 0 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-08-14 19:45:0014/08/2024 | Guisborough Town | 0 - 3 | Crook Town | Ebac Northern League Division 1 | |
| 2024-08-16 19:30:3616/08/2024 | Darlington R.A. | 3 - 0 | Guisborough Town Reserves | North Riding Mens Premier | |
| 2024-08-20 19:45:0020/08/2024 | Carlisle City | 1 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-08-23 19:30:5623/08/2024 | Guisborough Town Reserves | 1 - 2 |  Staithes Athletic | North Riding Mens Premier | |
| 2024-08-24 15:00:0024/08/2024 | Guisborough Town | 1 - 1 | Redcar Athletic | Ebac Northern League Division 1 | |
| 2024-08-28 19:45:0028/08/2024 | Guisborough Town | 5 - 1 | Birtley Town | Ebac Northern League Division 1 | |
| 2024-08-31 14:00:5731/08/2024 | Guisborough Town Reserves | 3 - 2 | Great Ayton United | North Riding Mens Premier | |
| 2024-08-31 15:00:0031/08/2024 | Easington Colliery  | 0 - 3 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-09-01 14:00:1701/09/2024 | Guisborough Town Ladies | 8 - 2 |  Cramlington United LFC | Adobe Women's FA Cup | |
| 2024-09-04 19:45:0004/09/2024 | Guisborough Town | 2 - 1 | Penrith | Ebac Northern League Division 1 | |
| 2024-09-07 14:00:1807/09/2024 | Stokesley Sports Club FC  | 2 - 0 | Guisborough Town Reserves | North Riding Mens Premier | |
| 2024-09-07 15:00:0007/09/2024 | Guisborough Town | 0 - 4 | West Auckland Town | Ebac Northern League Division 1 | |
| 2024-09-08 14:00:0008/09/2024 | Guisborough Town Ladies | 6 - 1 | York Railway Institute Ladies Reserves | North Riding Womens Premier League | |
| 2024-09-14 14:00:4114/09/2024 | Guisborough Town Reserves | 2 - 2 | T.I.B.S | North Riding Mens Premier | |
| 2024-09-14 15:00:4714/09/2024 | West Allotment Celtic | 0 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-09-15 14:00:0015/09/2024 | Redcar Athletic Ladies | 0 - 1 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2024-09-17 19:30:0017/09/2024 | Tow Law Town | 2 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-09-20 19:30:5720/09/2024 | Guisborough Town Reserves | 0 - 2 | Boro Rangers U23 | North Riding Mens Premier | |
| 2024-09-21 15:00:2021/09/2024 | Guisborough Town | 2 - 1 | Shildon | Isuzu FA Vase | |
| 2024-09-22 14:00:1222/09/2024 | Thornaby FC Ladies | 9 - 0 | Guisborough Town Ladies | Adobe Women's FA Cup | |
| 2024-09-28 15:00:0028/09/2024 | Guisborough Town | 3 - 2 | Whitley Bay | Ebac Northern League Division 1 | |
| 2024-09-29 14:00:0029/09/2024 | Guisborough Town Ladies | 3 - 3 | Richmond Town Women | North Riding Womens Premier League | |
| 2024-10-05 14:00:3105/10/2024 | Guisborough Town Reserves | 1 - 2 | Lealholm | North Riding Mens Premier | |
| 2024-10-05 15:00:0005/10/2024 | Shildon | 2 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-10-06 14:00:0006/10/2024 | Huntington Rovers Ladies | W - A | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2024-10-09 19:45:0009/10/2024 | Guisborough Town | 1 - 1 |  Blyth Town | Ebac Northern League Division 1 | |
| 2024-10-12 14:00:1412/10/2024 | Boro Rangers U23 | 3 - 2 | Guisborough Town Reserves | North Riding Mens Premier | |
| 2024-10-12 15:00:0012/10/2024 | Guisborough Town | 3 - 2 | Seaham Red Star | Ebac Northern League Division 1 | |
| 2024-10-13 14:00:0013/10/2024 | Guisborough Town Ladies | 1 - 1 | Linthorpe Academicals Women | North Riding Womens Premier League | |
| 2024-10-19 15:00:1819/10/2024 | Guisborough Town | 0 - 1 | Carlisle City | Isuzu FA Vase | |
| 2024-10-20 14:00:2820/10/2024 | Guisborough Town Ladies | 0 - 2 | York City Ladies Development | North Riding Womens Cup | |
| 2024-10-22 19:30:1722/10/2024 | Guisborough Town Reserves | 0 - 3 | Darlington R.A. | Macmillan Bowl | |
| 2024-10-23 19:45:0023/10/2024 | North Shields | 3 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-10-26 14:00:0426/10/2024 | Redcar Town Reserves | 1 - 4 | Guisborough Town Reserves | North Riding Mens Premier | |
| 2024-10-26 15:00:0026/10/2024 | Guisborough Town | 3 - 0 | Newcastle Benfield | Ebac Northern League Division 1 | |
| 2024-10-27 14:00:0027/10/2024 | York Railway Institute Ladies Reserves | 1 - 9 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2024-10-29 19:30:0029/10/2024 | Whickham | 0 - 4 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-11-02 14:00:4802/11/2024 | St Marys 1947 Dormans  | 3 - 1 | Guisborough Town Reserves | North Riding Mens Premier | |
| 2024-11-02 15:00:0002/11/2024 | Marske United | 1 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-11-03 14:00:0003/11/2024 | Guisborough Town Ladies | 3 - 2 | Redcar Athletic Ladies | North Riding Womens Premier League | |
| 2024-11-09 14:00:0809/11/2024 | Guisborough Town Reserves | 0 - 5 | Scarborough Athletic | WOODSmith Construction North Riding Saturday Challenge Cup | |
| 2024-11-09 15:00:0009/11/2024 | Guisborough Town | 3 - 2 | Kendal Town | Ebac Northern League Division 1 | |
| 2024-11-16 14:00:3216/11/2024 | Lealholm | 0 - 0 | Guisborough Town Reserves | North Riding Mens Premier | |
| 2024-11-16 15:00:0016/11/2024 | Guisborough Town | 3 - 2 | Whickham | Ebac Northern League Division 1 | |
| 2024-11-17 14:00:0017/11/2024 | Richmond Town Women | 1 - 2 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2024-11-30 14:00:3730/11/2024 | Kader | 2 - 0 | Guisborough Town Reserves | North Riding Mens Premier | |
| 2024-11-30 15:00:0030/11/2024 | Guisborough Town | 0 - 0 | Carlisle City | Ebac Northern League Division 1 | |
| 2024-12-01 14:00:0001/12/2024 | Linthorpe Academicals Women | 1 - 2 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2024-12-04 19:30:0004/12/2024 | Crook Town | 1 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-12-13 19:30:0013/12/2024 | Birtley Town | 1 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-12-14 14:00:1214/12/2024 | Staithes Athletic | 0 - 0 | Guisborough Town Reserves | North Riding Mens Premier | |
| 2024-12-15 14:00:0015/12/2024 | Northallerton Town Women | 2 - 3 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2024-12-18 19:45:2018/12/2024 | Guisborough Town | 3 - 1 | Pickering Town | WOODSmith Construction North Riding Senior Cup | |
| 2024-12-21 15:00:0021/12/2024 | Penrith | 0 - 2 | Guisborough Town | Ebac Northern League Division 1 | |
| 2024-12-26 12:00:0026/12/2024 | Guisborough Town | 2 - 3 | Boro Rangers | Ebac Northern League Division 1 | |
| 2024-12-28 15:00:0028/12/2024 | Guisborough Town | 4 - 1 | Tow Law Town | Ebac Northern League Division 1 | |
| 2025-01-04 15:00:0004/01/2025 | Boro Rangers | 0 - 4 | Guisborough Town | Ebac Northern League Division 1 | |
| 2025-01-18 14:00:5918/01/2025 | Guisborough Town Reserves | 1 - 2 | Darlington R.A. | North Riding Mens Premier | |
| 2025-01-18 15:00:0018/01/2025 | Redcar Athletic | 2 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2025-01-21 19:30:5621/01/2025 | West Allotment Celtic | 3 - 2 | Guisborough Town | Brooks Mileson Memorial Northern League Cup | |
| 2025-01-25 15:00:0025/01/2025 | Guisborough Town | 0 - 1 | Newcastle Blue Star | Ebac Northern League Division 1 | |
| 2025-01-26 14:00:0026/01/2025 | Guisborough Town Ladies | 9 - 1 | Northallerton Town Women | North Riding Womens Premier League | |
| 2025-01-29 19:45:0629/01/2025 | Middlesbrough U21/Reserves  | 3 - 1 | Guisborough Town | WOODSmith Construction North Riding Senior Cup | |
| 2025-02-01 14:00:3801/02/2025 | Guisborough Town Reserves | 2 - 2 | Redcar Athletic Reserves | North Riding Mens Premier | |
| 2025-02-02 14:00:0002/02/2025 | Guisborough Town Ladies | 8 - 0 | Huntington Rovers Ladies | North Riding Womens Premier League | |
| 2025-02-08 14:00:4308/02/2025 | Fishburn Park  | 2 - 4 | Guisborough Town Reserves | North Riding Mens Premier | |
| 2025-02-08 15:00:0008/02/2025 | Guisborough Town | 0 - 3 | Easington Colliery | Ebac Northern League Division 1 | |
| 2025-02-09 14:00:0009/02/2025 | Guisborough Town Ladies | 5 - 0 | Northallerton Town Women | North Riding Womens Premier League | |
| 2025-02-15 14:00:0615/02/2025 | Guisborough Town Reserves | 3 - 3 | St Marys 1947 Dormans | North Riding Mens Premier | |
| 2025-02-15 15:00:0015/02/2025 | West Auckland Town | 4 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2025-02-16 14:00:0016/02/2025 | Linthorpe Academicals Women | 1 - 1 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2025-02-22 14:00:1222/02/2025 | Yarm & Eaglescliffe FC Reserves | 5 - 0 | Guisborough Town Reserves | North Riding Mens Premier | |
| 2025-02-22 15:00:0022/02/2025 | Guisborough Town | 0 - 0 | West Allotment Celtic | Ebac Northern League Division 1 | |
| 2025-02-23 14:00:2323/02/2025 | Guisborough Town Ladies | H - W | Huntington Rovers Ladies | North Riding Womens Premier League | |
| 2025-02-26 19:45:0026/02/2025 | Guisborough Town | 1 - 2 | Northallerton Town | Ebac Northern League Division 1 | |
| 2025-03-01 14:00:5301/03/2025 | Guisborough Town Reserves | 0 - 2 | Kader | North Riding Mens Premier | |
| 2025-03-01 15:00:0001/03/2025 | Blyth Town | 1 - 3 | Guisborough Town | Ebac Northern League Division 1 | |
| 2025-03-02 14:00:0002/03/2025 | Redcar Athletic Ladies | 5 - 0 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2025-03-04 14:00:2904/03/2025 | Guisborough Town Reserves | 0 - 3 | Fishburn Park | North Riding Mens Premier | |
| 2025-03-08 14:00:0508/03/2025 | Guisborough Town Reserves | 0 - 2 | Yarm & Eaglescliffe FC Reserves | North Riding Mens Premier | |
| 2025-03-08 15:00:0008/03/2025 | Whitley Bay | 1 - 1 | Guisborough Town | Ebac Northern League Division 1 | |
| 2025-03-09 14:00:0009/03/2025 | Guisborough Town Ladies | 7 - 1 | Richmond Town Women | North Riding Womens Premier League | |
| 2025-03-15 14:00:0915/03/2025 | Great Ayton United | 1 - 1 | Guisborough Town Reserves | North Riding Mens Premier | |
| 2025-03-15 15:00:0015/03/2025 | Guisborough Town | 1 - 1 | Marske United | Ebac Northern League Division 1 | |
| 2025-03-16 14:00:0016/03/2025 | York Railway Institute Ladies Reserves | 0 - 8 | Guisborough Town Ladies | North Riding Womens Premier League | |
| 2025-03-22 15:00:0022/03/2025 | Seaham Red Star | 0 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2025-03-29 14:00:2129/03/2025 | Redcar Athletic Reserves | 0 - 2 | Guisborough Town Reserves | North Riding Mens Premier | |
| 2025-03-29 15:00:0029/03/2025 | Guisborough Town | 1 - 0 | Shildon | Ebac Northern League Division 1 | |
| 2025-04-01 19:30:4801/04/2025 | Guisborough Town Reserves | 3 - 1 | Stokesley Sports Club FC | North Riding Mens Premier | |
| 2025-04-05 14:00:5905/04/2025 | T.I.B.S | 2 - 1 | Guisborough Town Reserves | North Riding Mens Premier | |
| 2025-04-05 15:00:0005/04/2025 | Guisborough Town | 2 - 1 | North Shields | Ebac Northern League Division 1 | |
| 2025-04-12 14:00:1912/04/2025 | Guisborough Town Reserves | 1 - 1 | Redcar Town Reserves | North Riding Mens Premier | |
| 2025-04-12 15:00:0012/04/2025 | Newcastle Benfield | 1 - 0 | Guisborough Town | Ebac Northern League Division 1 | |
| 2025-05-10 15:00:0310/05/2025 | Guisborough Town Coaches Home | 15:00:0315:00 | Guisborough Town Coaches Away | | |
| 2025-07-19 15:00:1719/07/2025 | Guisborough Town | 15:00:1715:00 | Whitby Town | Micky Skinner Memorial Trophy | |
