| 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 | Vitality 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 RA | 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 | Copmanthorpe U16 | 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 | South Bank Albion | 6 - 0 | Guisborough Town Over 35s | 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 | Boro Rangers U16 | 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 | Boro Rangers U16 | 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 | Guisborough Town 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 | Guisborough Town 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 | Vitality 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 | Guisborough Town Ladies Reserves | North Riding Womens Premier League | |
| 2021-09-25 13:30:2225/09/2021 | Spennymoor Town | 13:30:2213:30 | Guisborough Town U18 | 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 | Guisborough Town 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 | Guisborough Town 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 Reserves | 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 | Guisborough Town 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 | Guisborough Town 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 | Guisborough Town 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 | 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 | Guisborough Town Ladies Reserves | 3 - 2 | Acklam Ladies | North Riding Womens Premier League | |
| 2021-11-13 14:00:5413/11/2021 | Boro Rangers Reserves | 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 | Guisborough Town 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 | 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 | 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 | Guisborough Town 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 14:00:5115/01/2022 | 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 | Guisborough Town 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 Reserves | 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 | Guisborough Town 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 FC | 3 - 4 | Guisborough Town | 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 | Guisborough Town 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 | Guisborough Town 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 | Guisborough Town 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 | Guisborough Town 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 | Guisborough Town 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 | Guisborough Town 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 | 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 | Guisborough Town 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 | Guisborough Town 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 | 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 | 15:00:3715:00 | Guisborough Town | Friendly | |
| 2022-07-06 19:45:0806/07/2022 | Guisborough Town | 19:45:0819:45 | Middlesbrough FC U23 | Friendly | |
| 2022-07-09 15:00:4009/07/2022 | Guisborough Town | 15:00:4015:00 | Marske United | John Butterfield Memorial Trophy | |
| 2022-07-13 19:45:5813/07/2022 | Thornaby | 19:45:5819:45 | Guisborough Town | Peter Morris Memorial Trophy | |
| 2022-07-20 19:45:2820/07/2022 | Stockton Town | 19:45:2819:45 | Guisborough Town | Friendly | |
| 2022-07-26 19:45:4726/07/2022 | Whitby Town | 19:45:4719:45 | Guisborough Town | Micky Skinner Memorial Trophy | |
| 2022-07-30 15:00:0030/07/2022 | Thornaby | 15:00:0015:00 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-08-02 19:45:0002/08/2022 | West Auckland Town | 19:45:0019:45 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-08-10 19:45:0010/08/2022 | Guisborough Town | 19:45:0019:45 | Newcastle Benfield | Ebac Northern League Division 1 | |
| 2022-08-16 19:45:0016/08/2022 | Guisborough Town | 19:45:0019:45 | Whickham | Ebac Northern League Division 1 | |
| 2022-08-20 15:00:0020/08/2022 | Guisborough Town | 15:00:0015:00 | West Allotment Celtic | Ebac Northern League Division 1 | |
| 2022-08-24 19:45:0024/08/2022 | Guisborough Town | 19:45:0019:45 | Tow Law Town | Ebac Northern League Division 1 | |
| 2022-08-30 19:45:0030/08/2022 | Newton Aycliffe | 19:45:0019:45 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-09-03 15:00:0003/09/2022 | Ashington | 15:00:0015:00 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-09-07 19:45:0007/09/2022 | Guisborough Town | 19:45:0019:45 | Heaton Stannington | Ebac Northern League Division 1 | |
| 2022-09-10 15:00:0010/09/2022 | Guisborough Town | 15:00:0015:00 | Whitley Bay | Ebac Northern League Division 1 | |
| 2022-09-17 15:00:0017/09/2022 | Carlisle City | 15:00:0015:00 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-10-01 15:00:0001/10/2022 | Penrith | 15:00:0015:00 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-10-04 19:45:0004/10/2022 | Guisborough Town | 19:45:0019:45 | Bishop Auckland | Ebac Northern League Division 1 | |
| 2022-10-08 15:00:0008/10/2022 | Guisborough Town | 15:00:0015:00 | Seaham Red Star | Ebac Northern League Division 1 | |
| 2022-10-12 19:45:0012/10/2022 | Crook Town | 19:45:0019:45 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-10-15 15:00:0015/10/2022 | Redcar Athletic | 15:00:0015:00 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-10-22 15:00:0022/10/2022 | Guisborough Town | 15:00:0015:00 | Crook Town | Ebac Northern League Division 1 | |
| 2022-10-29 15:00:0029/10/2022 | Pickering Town FC | 15:00:0015:00 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-11-05 15:00:0005/11/2022 | Guisborough Town | 15:00:0015:00 | Sunderland RCA | Ebac Northern League Division 1 | |
| 2022-11-12 15:00:0012/11/2022 | Guisborough Town | 15:00:0015:00 | West Auckland Town | Ebac Northern League Division 1 | |
| 2022-11-19 15:00:0019/11/2022 | Newcastle Benfield | 15:00:0015:00 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-11-26 15:00:0026/11/2022 | Whickham | 15:00:0015:00 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-12-10 15:00:0010/12/2022 | Tow Law Town | 15:00:0015:00 | Guisborough Town | Ebac Northern League Division 1 | |
| 2022-12-17 15:00:0017/12/2022 | Guisborough Town | 15:00:0015:00 | Newton Aycliffe | Ebac Northern League Division 1 | |
| 2022-12-26 19:45:0026/12/2022 | Guisborough Town | 19:45:0019:45 | Northallerton Town | Ebac Northern League Division 1 | |
| 2023-01-07 15:00:0007/01/2023 | Heaton Stannington | 15:00:0015:00 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-01-14 15:00:0014/01/2023 | Guisborough Town | 15:00:0015:00 | Thornaby | Ebac Northern League Division 1 | |
| 2023-01-21 15:00:0021/01/2023 | Bishop Auckland | 15:00:0015:00 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-02-04 15:00:0004/02/2023 | West Allotment Celtic | 15:00:0015:00 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-02-11 15:00:0011/02/2023 | Guisborough Town | 15:00:0015:00 | Ashington | Ebac Northern League Division 1 | |
| 2023-02-18 15:00:0018/02/2023 | Whitley Bay | 15:00:0015:00 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-02-25 15:00:0025/02/2023 | Guisborough Town | 15:00:0015:00 | Carlisle City | Ebac Northern League Division 1 | |
| 2023-03-11 15:00:0011/03/2023 | Guisborough Town | 15:00:0015:00 | Penrith | Ebac Northern League Division 1 | |
| 2023-03-18 15:00:0018/03/2023 | Seaham Red Star | 15:00:0015:00 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-03-25 15:00:0025/03/2023 | Guisborough Town | 15:00:0015:00 | Redcar Athletic | Ebac Northern League Division 1 | |
| 2023-04-07 19:45:0007/04/2023 | Northallerton Town | 19:45:0019:45 | Guisborough Town | Ebac Northern League Division 1 | |
| 2023-04-15 15:00:0015/04/2023 | Guisborough Town | 15:00:0015:00 | Pickering Town FC | Ebac Northern League Division 1 | |
| 2023-04-22 15:00:0022/04/2023 | Sunderland RCA | 15:00:0015:00 | Guisborough Town | Ebac Northern League Division 1 | |
