| 1 | Sat 27 Jul | 63-1 v Northallerton TownNorthallerton Town 1-3 Guisborough Town | Northern League Division One |
| 2 | Tue 30 Jul | 60-1 v Kendal TownKendal Town 1-0 Guisborough Town | Northern League Division One |
| 3 | Sat 3 Aug | 52-2 v Kendal TownKendal Town 2-2 Guisborough Town | Emirates FA Cup Extra Preliminary Round |
| 4 | Wed 7 Aug | 61-2 v Kendal TownGuisborough Town 1-2 Kendal Town | Emirates FA Cup Extra Preliminary Round Replay |
| 5 | Sat 10 Aug | 62-0 v Newcastle Blue StarNewcastle Blue Star 0-2 Guisborough Town | Northern League Division One |
| 6 | Wed 14 Aug | 30-3 v Crook TownGuisborough Town 0-3 Crook Town | Northern League Division One |
| 7 | Sat 24 Aug | 61-1 v Redcar AthleticGuisborough Town 1-1 Redcar Athletic | Northern League Division One |
| 8 | Sat 7 Sep | 20-4 v West Auckland TownGuisborough Town 0-4 West Auckland Town | Northern League Division One |
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