| 1 | Wed 30 Jul | 14 1-0 v Boro RangersGuisborough Town 1-0 Boro Rangers | Northern League Division One |
| 2 | Tue 5 Aug | 22-0 v Consett AFCConsett AFC 0-2 Guisborough Town | Emirates FA Cup Extra Preliminary Round Replay |
| 3 | Sat 9 Aug | 21-1 v West Auckland TownWest Auckland Town 1-1 Guisborough Town | Northern League Division One |
| 4 | Wed 13 Aug | 155-0 v Birtley TownGuisborough Town 5-0 Birtley Town | Northern League Division One |
| 5 | Sat 16 Aug | 20-0 v Redcar AthleticGuisborough Town 0-0 Redcar Athletic | Emirates FA Cup Preliminary Round |
| 6 | Wed 20 Aug | 20-1 v Redcar AthleticRedcar Athletic 1-0 Guisborough Town | Emirates FA Cup Preliminary Round Replay |
| 7 | Sat 4 Oct | 33-0 v Marske UnitedMarske United 0-3 Guisborough Town | Northern League Division One |
| 8 | Sat 11 Oct | 123-1 v Horden Community WelfareGuisborough Town 3-1 Horden Community Welfare | Northern League Division One |
| 9 | Sat 18 Oct | 2 3-3 v Newcastle Blue StarNewcastle Blue Star 3-3 Guisborough Town | Northern League Division One |
| 10 | Sat 8 Nov | 24-3 v ShildonGuisborough Town 4-3 Shildon | Northern League Division One |
| 11 | Sat 15 Nov | 24-1 v Easington CollieryGuisborough Town 4-1 Easington Colliery | Northern League Division One |
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