| 1 | Sat 12 Oct | 123-2 v Seaham Red StarGuisborough Town 3-2 Seaham Red Star | Northern League Division One |
| 2 | Sat 19 Oct | 70-1 v Carlisle CityGuisborough Town 0-1 Carlisle City | Isuzu FA Vase First Round |
| 3 | Wed 23 Oct | 71-3 v North ShieldsNorth Shields 3-1 Guisborough Town | Northern League Division One |
| 4 | Sat 26 Oct | 143-0 v Newcastle BenfieldGuisborough Town 3-0 Newcastle Benfield | Northern League Division One |
| 5 | Tue 29 Oct | 144-0 v WhickhamWhickham 0-4 Guisborough Town | Northern League Division One |
| 6 | Sat 2 Nov | 71-1 v Marske UnitedMarske United 1-1 Guisborough Town | Northern League Division One |
| 7 | Sat 9 Nov | 143-2 v Kendal TownGuisborough Town 3-2 Kendal Town | Northern League Division One |
| 8 | Sat 16 Nov | 143-2 v WhickhamGuisborough Town 3-2 Whickham | Northern League Division One |
| 9 | Sat 30 Nov | 70-0 v Carlisle CityGuisborough Town 0-0 Carlisle City | Northern League Division One |
| 10 | Fri 13 Dec | 121-1 v Birtley TownBirtley Town 1-1 Guisborough Town | Northern League Division One |
| 11 | Sat 21 Dec | 122-0 v PenrithPenrith 0-2 Guisborough Town | Northern League Division One |
| 12 | Thu 26 Dec | 72-3 v Boro RangersGuisborough Town 2-3 Boro Rangers | Northern League Division One |
| 13 | Sat 28 Dec | 74-1 v Tow Law TownGuisborough Town 4-1 Tow Law Town | Northern League Division One |
| 14 | Sat 18 Jan | 70-2 v Redcar AthleticRedcar Athletic 2-0 Guisborough Town | Northern League Division One |
| 15 | Sat 25 Jan | 110-1 v Newcastle Blue StarGuisborough Town 0-1 Newcastle Blue Star | Northern League Division One |
| 16 | Sat 15 Feb | 111-4 v West Auckland TownWest Auckland Town 4-1 Guisborough Town | Northern League Division One |
| 17 | Sat 22 Feb | 120-0 v West Allotment CelticGuisborough Town 0-0 West Allotment Celtic | Northern League Division One |
| 18 | Wed 26 Feb | 121-2 v Northallerton TownGuisborough Town 1-2 Northallerton Town | Northern League Division One |
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