| 1 | Wed 17 Sep | 92-1 v Whitley BayGuisborough Town 2-1 Whitley Bay | Northern League Division One |
| 2 | Sat 20 Sep | 92-1 v West Auckland TownGuisborough Town 2-1 West Auckland Town | Northern League Division One |
| 3 | Sat 27 Sep | 92-0 v Newcastle BenfieldGuisborough Town 2-0 Newcastle Benfield | Northern League Division One |
| 4 | Sat 4 Oct | 93-0 v Marske UnitedMarske United 0-3 Guisborough Town | Northern League Division One |
| 5 | Sat 11 Oct | 93-1 v Horden Community WelfareGuisborough Town 3-1 Horden Community Welfare | Northern League Division One |
| 6 | Sat 18 Oct | 93-3 v Newcastle Blue StarNewcastle Blue Star 3-3 Guisborough Town | Northern League Division One |
| 7 | Sat 25 Oct | 91-0 v Crook TownCrook Town 0-1 Guisborough Town | Northern League Division One |
| 8 | Sat 1 Nov | 92-2 v Carlisle CityGuisborough Town 2-2 Carlisle City | Northern League Division One |
| 9 | Sat 8 Nov | 94-3 v ShildonGuisborough Town 4-3 Shildon | Northern League Division One |
| 10 | Tue 11 Nov | 92-3 v Scarborough AthleticScarborough Athletic 3-2 Guisborough Town | North Riding Senior Cup |
| 11 | Sat 15 Nov | 9 4-1 v Easington CollieryGuisborough Town 4-1 Easington Colliery | Northern League Division One |
| 12 | Sat 13 Dec | 92-0 v Kendal TownKendal Town 0-2 Guisborough Town | Northern League Division One |
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