| 1 | Sat 31 Aug | 83-0 v Easington CollieryEasington Colliery 0-3 Guisborough Town | Northern League Division One |
| 2 | Sat 14 Sep | 80-0 v West Allotment CelticWest Allotment Celtic 0-0 Guisborough Town | Northern League Division One |
| 3 | Tue 17 Sep | 62-2 v Tow Law TownTow Law Town 2-2 Guisborough Town | Northern League Division One |
| 4 | Sat 28 Sep | 153-2 v Whitley BayGuisborough Town 3-2 Whitley Bay | Northern League Division One |
| 5 | Sat 5 Oct | 151-2 v ShildonShildon 2-1 Guisborough Town | Northern League Division One |
| 6 | Wed 9 Oct | 41-1 v Blyth TownGuisborough Town 1-1 Blyth Town | Northern League Division One |
| 7 | Sat 12 Oct | 43-2 v Seaham Red StarGuisborough Town 3-2 Seaham Red Star | Northern League Division One |
| 8 | Sat 19 Oct | 40-1 v Carlisle CityGuisborough Town 0-1 Carlisle City | Isuzu FA Vase First Round |
| 9 | Wed 23 Oct | 41-3 v North ShieldsNorth Shields 3-1 Guisborough Town | Northern League Division One |
| 10 | Sat 26 Oct | 123-0 v Newcastle BenfieldGuisborough Town 3-0 Newcastle Benfield | Northern League Division One |
| 11 | Tue 29 Oct | 124-0 v WhickhamWhickham 0-4 Guisborough Town | Northern League Division One |
| 12 | Sat 2 Nov | 121-1 v Marske UnitedMarske United 1-1 Guisborough Town | Northern League Division One |
| 13 | Sat 9 Nov | 123-2 v Kendal TownGuisborough Town 3-2 Kendal Town | Northern League Division One |
| 14 | Fri 13 Dec | 151-1 v Birtley TownBirtley Town 1-1 Guisborough Town | Northern League Division One |
| 15 | Sat 21 Dec | 92-0 v PenrithPenrith 0-2 Guisborough Town | Northern League Division One |
| 16 | Thu 26 Dec | 92-3 v Boro RangersGuisborough Town 2-3 Boro Rangers | Northern League Division One |
| 17 | Sat 28 Dec | 94-1 v Tow Law TownGuisborough Town 4-1 Tow Law Town | Northern League Division One |
| 18 | Sat 4 Jan | 94-0 v Boro RangersBoro Rangers 0-4 Guisborough Town | Northern League Division One |
| 19 | Sat 18 Jan | 90-2 v Redcar AthleticRedcar Athletic 2-0 Guisborough Town | Northern League Division One |
| 20 | Sat 25 Jan | 150-1 v Newcastle Blue StarGuisborough Town 0-1 Newcastle Blue Star | Northern League Division One |
| 21 | Sat 15 Feb | 41-4 v West Auckland TownWest Auckland Town 4-1 Guisborough Town | Northern League Division One |
| 22 | Sat 22 Feb | 40-0 v West Allotment CelticGuisborough Town 0-0 West Allotment Celtic | Northern League Division One |
| 23 | Wed 26 Feb | 91-2 v Northallerton TownGuisborough Town 1-2 Northallerton Town | Northern League Division One |
| 24 | Sat 1 Mar | 93-1 v Blyth TownBlyth Town 1-3 Guisborough Town | Northern League Division One |
| 25 | Sat 8 Mar | 91-1 v Whitley BayWhitley Bay 1-1 Guisborough Town | Northern League Division One |
| 26 | Sat 29 Mar | 151-1 v ShildonGuisborough Town 1-1 Shildon | Northern League Division One |
| 27 | Sat 5 Apr | 152-1 v North ShieldsGuisborough Town 2-1 North Shields | Northern League Division One |
| 28 | Sat 12 Apr | 140-1 v Newcastle BenfieldNewcastle Benfield 1-0 Guisborough Town | Northern League Division One |
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