| 1 | Wed 17 Sep | 122-1 v Whitley BayGuisborough Town 2-1 Whitley Bay | Northern League Division One |
| 2 | Sat 20 Sep | 112-1 v West Auckland TownGuisborough Town 2-1 West Auckland Town | Northern League Division One |
| 3 | Sat 4 Oct | 113-0 v Marske UnitedMarske United 0-3 Guisborough Town | Northern League Division One |
| 4 | Sat 11 Oct | 113-1 v Horden Community WelfareGuisborough Town 3-1 Horden Community Welfare | Northern League Division One |
| 5 | Sat 1 Nov | 142-2 v Carlisle CityGuisborough Town 2-2 Carlisle City | Northern League Division One |
| 6 | Sat 8 Nov | 8 4-3 v ShildonGuisborough Town 4-3 Shildon | Northern League Division One |
| 7 | Tue 11 Nov | 62-3 v Scarborough AthleticScarborough Athletic 3-2 Guisborough Town | North Riding Senior Cup |
| 8 | Sat 15 Nov | 64-1 v Easington CollieryGuisborough Town 4-1 Easington Colliery | Northern League Division One |
| 9 | Sat 22 Nov | 94-0 v Boro RangersBoro Rangers 0-4 Guisborough Town | Northern League Division One |
| 10 | Sat 13 Dec | 82-0 v Kendal TownKendal Town 0-2 Guisborough Town | Northern League Division One |
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