| 1 | Sat 16 Aug | 160-0 v Redcar AthleticGuisborough Town 0-0 Redcar Athletic | Emirates FA Cup Preliminary Round |
| 2 | Wed 20 Aug | 120-1 v Redcar AthleticRedcar Athletic 1-0 Guisborough Town | Emirates FA Cup Preliminary Round Replay |
| 3 | Tue 26 Aug | 80-1 v West Allotment CelticWest Allotment Celtic 1-0 Guisborough Town | Northern League Division One |
| 4 | Sat 30 Aug | 171-0 v WhickhamGuisborough Town 1-0 Whickham | Northern League Division One |
| 5 | Sat 6 Sep | 143-1 v Kendal TownGuisborough Town 3-1 Kendal Town | Northern League Division One |
| 6 | Wed 10 Sep | 142-0 v ThornabyGuisborough Town 2-0 Thornaby | Northern League Division One |
| 7 | Sat 13 Sep | 91-2 v PenrithPenrith 2-1 Guisborough Town | Northern League Division One |
| 8 | Sat 20 Sep | 162-1 v West Auckland TownGuisborough Town 2-1 West Auckland Town | Northern League Division One |
| 9 | Sat 27 Sep | 82-0 v Newcastle BenfieldGuisborough Town 2-0 Newcastle Benfield | Northern League Division One |
| 10 | Sat 4 Oct | 163-0 v Marske UnitedMarske United 0-3 Guisborough Town | Northern League Division One |
| 11 | Sat 11 Oct | 153-1 v Horden Community WelfareGuisborough Town 3-1 Horden Community Welfare | Northern League Division One |
| 12 | Sat 18 Oct | 83-3 v Newcastle Blue StarNewcastle Blue Star 3-3 Guisborough Town | Northern League Division One |
| 13 | Sat 8 Nov | 154-3 v ShildonGuisborough Town 4-3 Shildon | Northern League Division One |
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