| 1 | Tue 30 Jul | 90-1 v Kendal TownKendal Town 1-0 Guisborough Town | Northern League Division One |
| 2 | Wed 7 Aug | 101-2 v Kendal TownGuisborough Town 1-2 Kendal Town | Emirates FA Cup Extra Preliminary Round Replay |
| 3 | Wed 14 Aug | 120-3 v Crook TownGuisborough Town 0-3 Crook Town | Northern League Division One |
| 4 | Wed 28 Aug | 95-1 v Birtley TownGuisborough Town 5-1 Birtley Town | Northern League Division One |
| 5 | Wed 4 Sep | 92-1 v PenrithGuisborough Town 2-1 Penrith | Northern League Division One |
| 6 | Sat 7 Sep | 90-4 v West Auckland TownGuisborough Town 0-4 West Auckland Town | Northern League Division One |
| 7 | Sat 14 Sep | 9 0-0 v West Allotment CelticWest Allotment Celtic 0-0 Guisborough Town | Northern League Division One |
| 8 | Tue 17 Sep | 142-2 v Tow Law TownTow Law Town 2-2 Guisborough Town | Northern League Division One |
| 9 | Sat 21 Sep | 9 2-1 v ShildonGuisborough Town 2-1 Shildon | Isuzu FA Vase Second Qualifying Round |
| 10 | Sat 28 Sep | 73-2 v Whitley BayGuisborough Town 3-2 Whitley Bay | Northern League Division One |
| 11 | Sat 5 Oct | 101-2 v ShildonShildon 2-1 Guisborough Town | Northern League Division One |
| 12 | Wed 9 Oct | 91-1 v Blyth TownGuisborough Town 1-1 Blyth Town | Northern League Division One |
| 13 | Sat 12 Oct | 93-2 v Seaham Red StarGuisborough Town 3-2 Seaham Red Star | Northern League Division One |
| 14 | Sat 19 Oct | 90-1 v Carlisle CityGuisborough Town 0-1 Carlisle City | Isuzu FA Vase First Round |
| 15 | Wed 23 Oct | 141-3 v North ShieldsNorth Shields 3-1 Guisborough Town | Northern League Division One |
| 16 | Sat 26 Oct | 73-0 v Newcastle BenfieldGuisborough Town 3-0 Newcastle Benfield | Northern League Division One |
| 17 | Tue 29 Oct | 9 4-0 v WhickhamWhickham 0-4 Guisborough Town | Northern League Division One |
| 18 | Sat 2 Nov | 9 1-1 v Marske UnitedMarske United 1-1 Guisborough Town | Northern League Division One |
| 19 | Sat 9 Nov | 73-2 v Kendal TownGuisborough Town 3-2 Kendal Town | Northern League Division One |
| 20 | Sat 16 Nov | 73-2 v WhickhamGuisborough Town 3-2 Whickham | Northern League Division One |
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