| 1 | Sat 27 Jul | 143-1 v Northallerton TownNorthallerton Town 1-3 Guisborough Town | Northern League Division One |
| 2 | Tue 30 Jul | 120-1 v Kendal TownKendal Town 1-0 Guisborough Town | Northern League Division One |
| 3 | Sat 3 Aug | 10 2-2 v Kendal TownKendal Town 2-2 Guisborough Town | Emirates FA Cup Extra Preliminary Round |
| 4 | Wed 7 Aug | 91-2 v Kendal TownGuisborough Town 1-2 Kendal Town | Emirates FA Cup Extra Preliminary Round Replay |
| 5 | Sat 10 Aug | 9 2-0 v Newcastle Blue StarNewcastle Blue Star 0-2 Guisborough Town | Northern League Division One |
| 6 | Wed 14 Aug | 90-3 v Crook TownGuisborough Town 0-3 Crook Town | Northern League Division One |
| 7 | Tue 20 Aug | 91-1 v Carlisle CityCarlisle City 1-1 Guisborough Town | Northern League Division One |
| 8 | Sat 24 Aug | 91-1 v Redcar AthleticGuisborough Town 1-1 Redcar Athletic | Northern League Division One |
| 9 | Sat 31 Aug | 93-0 v Easington CollieryEasington Colliery 0-3 Guisborough Town | Northern League Division One |
| 10 | Sat 14 Sep | 140-0 v West Allotment CelticWest Allotment Celtic 0-0 Guisborough Town | Northern League Division One |
| 11 | Tue 17 Sep | 92-2 v Tow Law TownTow Law Town 2-2 Guisborough Town | Northern League Division One |
| 12 | Sat 21 Sep | 102-1 v ShildonGuisborough Town 2-1 Shildon | Isuzu FA Vase Second Qualifying Round |
| 13 | Sat 28 Sep | 93-2 v Whitley BayGuisborough Town 3-2 Whitley Bay | Northern League Division One |
| 14 | Sat 5 Oct | 9 1-2 v ShildonShildon 2-1 Guisborough Town | Northern League Division One |
| 15 | Sat 19 Oct | 120-1 v Carlisle CityGuisborough Town 0-1 Carlisle City | Isuzu FA Vase First Round |
| 16 | Wed 23 Oct | 9 1-3 v North ShieldsNorth Shields 3-1 Guisborough Town | Northern League Division One |
| 17 | Sat 26 Oct | 93-0 v Newcastle BenfieldGuisborough Town 3-0 Newcastle Benfield | Northern League Division One |
| 18 | Sat 9 Nov | 93-2 v Kendal TownGuisborough Town 3-2 Kendal Town | Northern League Division One |
| 19 | Sat 16 Nov | 93-2 v WhickhamGuisborough Town 3-2 Whickham | Northern League Division One |
| 20 | Sat 30 Nov | 90-0 v Carlisle CityGuisborough Town 0-0 Carlisle City | Northern League Division One |
| 21 | Wed 4 Dec | 91-1 v Crook TownCrook Town 1-1 Guisborough Town | Northern League Division One |
| 22 | Sat 25 Jan | 100-1 v Newcastle Blue StarGuisborough Town 0-1 Newcastle Blue Star | Northern League Division One |
| 23 | Sat 15 Feb | 171-4 v West Auckland TownWest Auckland Town 4-1 Guisborough Town | Northern League Division One |
| 24 | Sat 22 Feb | 9 0-0 v West Allotment CelticGuisborough Town 0-0 West Allotment Celtic | Northern League Division One |
| 25 | Wed 26 Feb | 171-2 v Northallerton TownGuisborough Town 1-2 Northallerton Town | Northern League Division One |
| 26 | Sat 22 Mar | 90-0 v Seaham Red StarSeaham Red Star 0-0 Guisborough Town | Northern League Division One |
| 27 | Sat 29 Mar | 91-1 v ShildonGuisborough Town 1-1 Shildon | Northern League Division One |
| 28 | Sat 5 Apr | 92-1 v North ShieldsGuisborough Town 2-1 North Shields | Northern League Division One |
| 29 | Sat 12 Apr | 90-1 v Newcastle BenfieldNewcastle Benfield 1-0 Guisborough Town | Northern League Division One |
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