2024-08-16 19:30:3616/08/2024 | Darlington R.A.  | 3 - 0 | Guisborough Town Reserves | North Riding Mens Premier | |
2024-08-23 19:30:5623/08/2024 | Guisborough Town Reserves  | 1 - 2 | Staithes Athletic | North Riding Mens Premier | |
2024-08-31 14:00:5731/08/2024 | Guisborough Town Reserves  | 3 - 2 | Great Ayton United | North Riding Mens Premier | |
2024-09-07 14:00:1807/09/2024 | Stokesley Sports Club FC  | 2 - 0 | Guisborough Town Reserves | North Riding Mens Premier | |
2024-09-14 14:00:4114/09/2024 | Guisborough Town Reserves  | 2 - 2 | T.I.B.S | North Riding Mens Premier | |
2024-09-20 19:30:5720/09/2024 | Guisborough Town Reserves  | 0 - 2 | Boro Rangers U23 | North Riding Mens Premier | |
2024-10-05 14:00:3105/10/2024 | Guisborough Town Reserves  | 1 - 2 | Lealholm | North Riding Mens Premier | |
2024-10-12 14:00:1412/10/2024 | Boro Rangers U23  | 3 - 2 | Guisborough Town Reserves | North Riding Mens Premier | |
2024-10-22 19:30:1722/10/2024 | Guisborough Town Reserves  | 0 - 3 | Darlington R.A. | Macmillan Bowl | |
2024-10-26 14:00:0426/10/2024 | Redcar Town Reserves  | 1 - 4 | Guisborough Town Reserves | North Riding Mens Premier | |
2024-11-02 14:00:4802/11/2024 | St Marys 1947 Dormans  | 3 - 1 | Guisborough Town Reserves | North Riding Mens Premier | |
2024-11-09 14:00:0809/11/2024 | Guisborough Town Reserves  | 0 - 5 | Scarborough Athletic | WOODSmith Construction North Riding Saturday Challenge Cup | |
2024-11-16 14:00:3216/11/2024 | Lealholm  | 0 - 0 | Guisborough Town Reserves | North Riding Mens Premier | |
2024-11-30 14:00:3730/11/2024 | Kader  | 2 - 0 | Guisborough Town Reserves | North Riding Mens Premier | |
2024-12-14 14:00:1214/12/2024 | Staithes Athletic  | 0 - 0 | Guisborough Town Reserves | North Riding Mens Premier | |
2025-01-18 14:00:5918/01/2025 | Guisborough Town Reserves  | 1 - 2 | Darlington R.A. | North Riding Mens Premier | |
2025-02-01 14:00:3801/02/2025 | Guisborough Town Reserves  | 2 - 2 | Redcar Athletic Reserves | North Riding Mens Premier | |
2025-02-08 14:00:4308/02/2025 | Fishburn Park  | 2 - 4 | Guisborough Town Reserves | North Riding Mens Premier | |
2025-02-15 14:00:0615/02/2025 | Guisborough Town Reserves  | 3 - 3 | St Marys 1947 Dormans | North Riding Mens Premier | |
2025-02-22 14:00:1222/02/2025 | Yarm & Eaglescliffe FC Reserves  | 5 - 0 | Guisborough Town Reserves | North Riding Mens Premier | |
2025-03-01 14:00:5301/03/2025 | Guisborough Town Reserves  | 0 - 2 | Kader | North Riding Mens Premier | |
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 | |
2025-03-15 14:00:0915/03/2025 | Great Ayton United  | 1 - 1 | Guisborough Town Reserves | North Riding Mens Premier | |
2025-03-29 14:00:2129/03/2025 | Redcar Athletic Reserves  | 0 - 2 | Guisborough Town Reserves | North Riding Mens Premier | |
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 | |
2025-04-12 14:00:1912/04/2025 | Guisborough Town Reserves  | 1 - 1 | Redcar Town Reserves | North Riding Mens Premier | |