| 1 | Wed 9 Oct | 81-1 v Blyth TownGuisborough Town 1-1 Blyth Town | Northern League Division One |
| 2 | Sat 12 Oct | 83-2 v Seaham Red StarGuisborough Town 3-2 Seaham Red Star | Northern League Division One |
| 3 | Sat 19 Oct | 80-1 v Carlisle CityGuisborough Town 0-1 Carlisle City | Isuzu FA Vase First Round |
| 4 | Sat 26 Oct | 83-0 v Newcastle BenfieldGuisborough Town 3-0 Newcastle Benfield | Northern League Division One |
| 5 | Tue 29 Oct | 84-0 v WhickhamWhickham 0-4 Guisborough Town | Northern League Division One |
| 6 | Sat 2 Nov | 81-1 v Marske UnitedMarske United 1-1 Guisborough Town | Northern League Division One |
| 7 | Sat 9 Nov | 83-2 v Kendal TownGuisborough Town 3-2 Kendal Town | Northern League Division One |
| 8 | Sat 16 Nov | 103-2 v WhickhamGuisborough Town 3-2 Whickham | Northern League Division One |
| 9 | Sat 30 Nov | 100-0 v Carlisle CityGuisborough Town 0-0 Carlisle City | Northern League Division One |
| 10 | Sat 21 Dec | 162-0 v PenrithPenrith 0-2 Guisborough Town | Northern League Division One |
| 11 | Sat 18 Jan | 170-2 v Redcar AthleticRedcar Athletic 2-0 Guisborough Town | Northern League Division One |
| 12 | Sat 25 Jan | 80-1 v Newcastle Blue StarGuisborough Town 0-1 Newcastle Blue Star | Northern League Division One |
| 13 | Sat 22 Feb | 100-0 v West Allotment CelticGuisborough Town 0-0 West Allotment Celtic | Northern League Division One |
| 14 | Wed 26 Feb | 101-2 v Northallerton TownGuisborough Town 1-2 Northallerton Town | Northern League Division One |
| 15 | Sat 1 Mar | 143-1 v Blyth TownBlyth Town 1-3 Guisborough Town | Northern League Division One |
| 16 | Sat 8 Mar | 151-1 v Whitley BayWhitley Bay 1-1 Guisborough Town | Northern League Division One |
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