| 1 | Sat 11 Oct | 73-1 v Horden Community WelfareGuisborough Town 3-1 Horden Community Welfare | Northern League Division One |
| 2 | Sat 18 Oct | 73-3 v Newcastle Blue StarNewcastle Blue Star 3-3 Guisborough Town | Northern League Division One |
| 3 | Sat 25 Oct | 71-0 v Crook TownCrook Town 0-1 Guisborough Town | Northern League Division One |
| 4 | Sat 1 Nov | 72-2 v Carlisle CityGuisborough Town 2-2 Carlisle City | Northern League Division One |
| 5 | Sat 8 Nov | 74-3 v ShildonGuisborough Town 4-3 Shildon | Northern League Division One |
| 6 | Tue 11 Nov | 102-3 v Scarborough AthleticScarborough Athletic 3-2 Guisborough Town | North Riding Senior Cup |
| 7 | Sat 15 Nov | 84-1 v Easington CollieryGuisborough Town 4-1 Easington Colliery | Northern League Division One |
| 8 | Sat 22 Nov | 104-0 v Boro RangersBoro Rangers 0-4 Guisborough Town | Northern League Division One |
| 9 | Sat 13 Dec | 102-0 v Kendal TownKendal Town 0-2 Guisborough Town | Northern League Division One |
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