| 1 | Sat 27 Jul | 43-1 v Northallerton TownNorthallerton Town 1-3 Guisborough Town | Northern League Division One |
| 2 | Sat 3 Aug | 4 2-2 v Kendal TownKendal Town 2-2 Guisborough Town | Emirates FA Cup Extra Preliminary Round |
| 3 | Wed 7 Aug | 71-2 v Kendal TownGuisborough Town 1-2 Kendal Town | Emirates FA Cup Extra Preliminary Round Replay |
| 4 | Sat 10 Aug | 4 2-0 v Newcastle Blue StarNewcastle Blue Star 0-2 Guisborough Town | Northern League Division One |
| 5 | Wed 14 Aug | 40-3 v Crook TownGuisborough Town 0-3 Crook Town | Northern League Division One |
| 6 | Wed 28 Aug | 45-1 v Birtley TownGuisborough Town 5-1 Birtley Town | Northern League Division One |
| 7 | Wed 4 Sep | 42-1 v PenrithGuisborough Town 2-1 Penrith | Northern League Division One |
| 8 | Sat 7 Sep | 4 0-4 v West Auckland TownGuisborough Town 0-4 West Auckland Town | Northern League Division One |
| 9 | Sat 21 Sep | 62-1 v ShildonGuisborough Town 2-1 Shildon | Isuzu FA Vase Second Qualifying Round |
| 10 | Sat 28 Sep | 43-2 v Whitley BayGuisborough Town 3-2 Whitley Bay | Northern League Division One |
| 11 | Sat 5 Oct | 41-2 v ShildonShildon 2-1 Guisborough Town | Northern League Division One |
| 12 | Sat 12 Oct | 153-2 v Seaham Red StarGuisborough Town 3-2 Seaham Red Star | Northern League Division One |
| 13 | Sat 19 Oct | 150-1 v Carlisle CityGuisborough Town 0-1 Carlisle City | Isuzu FA Vase First Round |
| 14 | Sat 2 Nov | 51-1 v Marske UnitedMarske United 1-1 Guisborough Town | Northern League Division One |
| 15 | Sat 9 Nov | 173-2 v Kendal TownGuisborough Town 3-2 Kendal Town | Northern League Division One |
| 16 | Sat 16 Nov | 173-2 v WhickhamGuisborough Town 3-2 Whickham | Northern League Division One |
| 17 | Thu 26 Dec | 62-3 v Boro RangersGuisborough Town 2-3 Boro Rangers | Northern League Division One |
| 18 | Sat 28 Dec | 154-1 v Tow Law TownGuisborough Town 4-1 Tow Law Town | Northern League Division One |
| 19 | Sat 4 Jan | 154-0 v Boro RangersBoro Rangers 0-4 Guisborough Town | Northern League Division One |
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