| 1 | Tue 11 Nov | 32-3 v Scarborough AthleticScarborough Athletic 3-2 Guisborough Town | North Riding Senior Cup |
| 2 | Sat 15 Nov | 164-1 v Easington CollieryGuisborough Town 4-1 Easington Colliery | Northern League Division One |
| 3 | Sat 22 Nov | 124-0 v Boro RangersBoro Rangers 0-4 Guisborough Town | Northern League Division One |
| 4 | Sat 13 Dec | 3 2-0 v Kendal TownKendal Town 0-2 Guisborough Town | Northern League Division One |
| 5 | Wed 17 Dec | 153-2 v West Allotment CelticGuisborough Town 3-2 West Allotment Celtic | Northern League Division One |
| 6 | Sat 20 Dec | 143-0 v North ShieldsNorth Shields 0-3 Guisborough Town | Northern League Division One |
| 7 | Fri 26 Dec | 142-1 v Northallerton TownGuisborough Town 2-1 Northallerton Town | Northern League Division One |
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