| 1 | Sat 27 Jul | 33-1 v Northallerton TownNorthallerton Town 1-3 Guisborough Town | Northern League Division One |
| 2 | Sat 3 Aug | 14 2-2 v Kendal TownKendal Town 2-2 Guisborough Town | Emirates FA Cup Extra Preliminary Round |
| 3 | Sat 10 Aug | 32-0 v Newcastle Blue StarNewcastle Blue Star 0-2 Guisborough Town | Northern League Division One |
| 4 | Tue 20 Aug | 61-1 v Carlisle CityCarlisle City 1-1 Guisborough Town | Northern League Division One |
| 5 | Sat 24 Aug | 31-1 v Redcar AthleticGuisborough Town 1-1 Redcar Athletic | Northern League Division One |
| 6 | Wed 28 Aug | 35-1 v Birtley TownGuisborough Town 5-1 Birtley Town | Northern League Division One |
| 7 | Sat 7 Sep | 12 0-4 v West Auckland TownGuisborough Town 0-4 West Auckland Town | Northern League Division One |
| 8 | Sat 14 Sep | 60-0 v West Allotment CelticWest Allotment Celtic 0-0 Guisborough Town | Northern League Division One |
| 9 | Wed 9 Oct | 111-1 v Blyth TownGuisborough Town 1-1 Blyth Town | Northern League Division One |
| 10 | Sat 26 Oct | 153-0 v Newcastle BenfieldGuisborough Town 3-0 Newcastle Benfield | Northern League Division One |
| 11 | Tue 29 Oct | 154-0 v WhickhamWhickham 0-4 Guisborough Town | Northern League Division One |
| 12 | Sat 2 Nov | 21-1 v Marske UnitedMarske United 1-1 Guisborough Town | Northern League Division One |
| 13 | Sat 9 Nov | 23-2 v Kendal TownGuisborough Town 3-2 Kendal Town | Northern League Division One |
| 14 | Sat 16 Nov | 23-2 v WhickhamGuisborough Town 3-2 Whickham | Northern League Division One |
| 15 | Sat 30 Nov | 60-0 v Carlisle CityGuisborough Town 0-0 Carlisle City | Northern League Division One |
| 16 | Wed 4 Dec | 31-1 v Crook TownCrook Town 1-1 Guisborough Town | Northern League Division One |
| 17 | Fri 13 Dec | 21-1 v Birtley TownBirtley Town 1-1 Guisborough Town | Northern League Division One |
| 18 | Sat 21 Dec | 22-0 v PenrithPenrith 0-2 Guisborough Town | Northern League Division One |
| 19 | Thu 26 Dec | 22-3 v Boro RangersGuisborough Town 2-3 Boro Rangers | Northern League Division One |
| 20 | Sat 4 Jan | 74-0 v Boro RangersBoro Rangers 0-4 Guisborough Town | Northern League Division One |
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