| 1 | Sat 27 Jul | 8 3-1 v Northallerton TownNorthallerton Town 1-3 Guisborough Town | Northern League Division One |
| 2 | Tue 30 Jul | 8 0-1 v Kendal TownKendal Town 1-0 Guisborough Town | Northern League Division One |
| 3 | Sat 3 Aug | 3 2-2 v Kendal TownKendal Town 2-2 Guisborough Town | Emirates FA Cup Extra Preliminary Round |
| 4 | Wed 7 Aug | 111-2 v Kendal TownGuisborough Town 1-2 Kendal Town | Emirates FA Cup Extra Preliminary Round Replay |
| 5 | Sat 10 Aug | 82-0 v Newcastle Blue StarNewcastle Blue Star 0-2 Guisborough Town | Northern League Division One |
| 6 | Tue 20 Aug | 7 1-1 v Carlisle CityCarlisle City 1-1 Guisborough Town | Northern League Division One |
| 7 | Sat 24 Aug | 111-1 v Redcar AthleticGuisborough Town 1-1 Redcar Athletic | Northern League Division One |
| 8 | Wed 28 Aug | 85-1 v Birtley TownGuisborough Town 5-1 Birtley Town | Northern League Division One |
| 9 | Sat 31 Aug | 43-0 v Easington CollieryEasington Colliery 0-3 Guisborough Town | Northern League Division One |
| 10 | Wed 4 Sep | 82-1 v PenrithGuisborough Town 2-1 Penrith | Northern League Division One |
| 11 | Sat 7 Sep | 80-4 v West Auckland TownGuisborough Town 0-4 West Auckland Town | Northern League Division One |
| 12 | Sat 14 Sep | 40-0 v West Allotment CelticWest Allotment Celtic 0-0 Guisborough Town | Northern League Division One |
| 13 | Tue 17 Sep | 52-2 v Tow Law TownTow Law Town 2-2 Guisborough Town | Northern League Division One |
| 14 | Sat 21 Sep | 32-1 v ShildonGuisborough Town 2-1 Shildon | Isuzu FA Vase Second Qualifying Round |
| 15 | Sat 28 Sep | 2 3-2 v Whitley BayGuisborough Town 3-2 Whitley Bay | Northern League Division One |
| 16 | Sat 5 Oct | 71-2 v ShildonShildon 2-1 Guisborough Town | Northern League Division One |
| 17 | Wed 9 Oct | 151-1 v Blyth TownGuisborough Town 1-1 Blyth Town | Northern League Division One |
| 18 | Sat 12 Oct | 2 3-2 v Seaham Red StarGuisborough Town 3-2 Seaham Red Star | Northern League Division One |
| 19 | Wed 23 Oct | 2 1-3 v North ShieldsNorth Shields 3-1 Guisborough Town | Northern League Division One |
| 20 | Sat 26 Oct | 23-0 v Newcastle BenfieldGuisborough Town 3-0 Newcastle Benfield | Northern League Division One |
| 21 | Tue 29 Oct | 24-0 v WhickhamWhickham 0-4 Guisborough Town | Northern League Division One |
| 22 | Sat 9 Nov | 153-2 v Kendal TownGuisborough Town 3-2 Kendal Town | Northern League Division One |
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