| 1 | Tue 11 Aug | 9 1-1 v Heaton StanningtonHeaton Stannington 1-1 Guisborough Town | Northern Premier League - East Division |
| 2 | Sat 15 Aug | 91-3 v Bradford (Park Avenue)Guisborough Town 1-3 Bradford (Park Avenue) | Northern Premier League - East Division |
| 3 | Sat 22 Aug | 122-0 v HallamGuisborough Town 2-0 Hallam | Northern Premier League - East Division |
| 4 | Mon 31 Aug | 102-0 v Consett AFCGuisborough Town 2-0 Consett AFC | Northern Premier League - East Division |
| 5 | Sat 5 Sep | 10 0-0 v Grimsby BoroughGrimsby Borough 0-0 Guisborough Town | Northern Premier League - East Division |
| 6 | Wed 16 Sep | 9 1-2 v Morpeth TownGuisborough Town 1-2 Morpeth Town | Northern Premier League - East Division |
| 7 | Sat 3 Oct | 100-4 v SilsdenSilsden 4-0 Guisborough Town | Northern Premier League - East Division |
| 8 | Sat 10 Oct | 9 0-1 v Blyth SpartansGuisborough Town 0-1 Blyth Spartans | Northern Premier League - East Division |
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