| 1 | Sat 27 Jul | 123-1 v Northallerton TownNorthallerton Town 1-3 Guisborough Town | Northern League Division One |
| 2 | Tue 30 Jul | 110-1 v Kendal TownKendal Town 1-0 Guisborough Town | Northern League Division One |
| 3 | Sat 3 Aug | 82-2 v Kendal TownKendal Town 2-2 Guisborough Town | Emirates FA Cup Extra Preliminary Round |
| 4 | Wed 14 Aug | 100-3 v Crook TownGuisborough Town 0-3 Crook Town | Northern League Division One |
| 5 | Tue 20 Aug | 41-1 v Carlisle CityCarlisle City 1-1 Guisborough Town | Northern League Division One |
| 6 | Sat 24 Aug | 81-1 v Redcar AthleticGuisborough Town 1-1 Redcar Athletic | Northern League Division One |
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