| 1 | Sat 27 Jul | 23-1 v Northallerton TownNorthallerton Town 1-3 Guisborough Town | Northern League Division One |
| 2 | Tue 30 Jul | 50-1 v Kendal TownKendal Town 1-0 Guisborough Town | Northern League Division One |
| 3 | Sat 3 Aug | 22-2 v Kendal TownKendal Town 2-2 Guisborough Town | Emirates FA Cup Extra Preliminary Round |
| 4 | Sat 10 Aug | 2 2-0 v Newcastle Blue StarNewcastle Blue Star 0-2 Guisborough Town | Northern League Division One |
| 5 | Wed 14 Aug | 20-3 v Crook TownGuisborough Town 0-3 Crook Town | Northern League Division One |
| 6 | Sat 24 Aug | 21-1 v Redcar AthleticGuisborough Town 1-1 Redcar Athletic | Northern League Division One |
| 7 | Wed 28 Aug | 25-1 v Birtley TownGuisborough Town 5-1 Birtley Town | Northern League Division One |
| 8 | Sat 31 Aug | 23-0 v Easington CollieryEasington Colliery 0-3 Guisborough Town | Northern League Division One |
| 9 | Wed 4 Sep | 22-1 v PenrithGuisborough Town 2-1 Penrith | Northern League Division One |
| 10 | Sat 14 Sep | 20-0 v West Allotment CelticWest Allotment Celtic 0-0 Guisborough Town | Northern League Division One |
| 11 | Sat 5 Oct | 21-2 v ShildonShildon 2-1 Guisborough Town | Northern League Division One |
| 12 | Wed 9 Oct | 21-1 v Blyth TownGuisborough Town 1-1 Blyth Town | Northern League Division One |
| 13 | Sat 26 Oct | 163-0 v Newcastle BenfieldGuisborough Town 3-0 Newcastle Benfield | Northern League Division One |
| 14 | Thu 26 Dec | 122-3 v Boro RangersGuisborough Town 2-3 Boro Rangers | Northern League Division One |
| 15 | Sat 28 Dec | 24-1 v Tow Law TownGuisborough Town 4-1 Tow Law Town | Northern League Division One |
| 16 | Sat 4 Jan | 24-0 v Boro RangersBoro Rangers 0-4 Guisborough Town | Northern League Division One |
| 17 | Sat 25 Jan | 20-1 v Newcastle Blue StarGuisborough Town 0-1 Newcastle Blue Star | Northern League Division One |
| 18 | Sat 15 Feb | 21-4 v West Auckland TownWest Auckland Town 4-1 Guisborough Town | Northern League Division One |
| 19 | Sat 22 Feb | 50-0 v West Allotment CelticGuisborough Town 0-0 West Allotment Celtic | Northern League Division One |
| 20 | Wed 26 Feb | 21-2 v Northallerton TownGuisborough Town 1-2 Northallerton Town | Northern League Division One |
| 21 | Sat 1 Mar | 23-1 v Blyth TownBlyth Town 1-3 Guisborough Town | Northern League Division One |
| 22 | Sat 8 Mar | 21-1 v Whitley BayWhitley Bay 1-1 Guisborough Town | Northern League Division One |
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