| 1 | Sat 26 Jul | 12-1 v Easington CollieryEasington Colliery 1-2 Guisborough Town | Northern League Division One |
| 2 | Wed 30 Jul | 11-0 v Boro RangersGuisborough Town 1-0 Boro Rangers | Northern League Division One |
| 3 | Sat 2 Aug | 12-2 v Consett AFCGuisborough Town 2-2 Consett AFC | Emirates FA Cup Extra Preliminary Round |
| 4 | Tue 5 Aug | 1 2-0 v Consett AFCConsett AFC 0-2 Guisborough Town | Emirates FA Cup Extra Preliminary Round Replay |
| 5 | Sat 9 Aug | 11-1 v West Auckland TownWest Auckland Town 1-1 Guisborough Town | Northern League Division One |
| 6 | Wed 13 Aug | 15-0 v Birtley TownGuisborough Town 5-0 Birtley Town | Northern League Division One |
| 7 | Sat 16 Aug | 10-0 v Redcar AthleticGuisborough Town 0-0 Redcar Athletic | Emirates FA Cup Preliminary Round |
| 8 | Wed 20 Aug | 10-1 v Redcar AthleticRedcar Athletic 1-0 Guisborough Town | Emirates FA Cup Preliminary Round Replay |
| 9 | Tue 26 Aug | 10-1 v West Allotment CelticWest Allotment Celtic 1-0 Guisborough Town | Northern League Division One |
| 10 | Sat 30 Aug | 11-0 v WhickhamGuisborough Town 1-0 Whickham | Northern League Division One |
| 11 | Sat 6 Sep | 13-1 v Kendal TownGuisborough Town 3-1 Kendal Town | Northern League Division One |
| 12 | Wed 10 Sep | 12-0 v ThornabyGuisborough Town 2-0 Thornaby | Northern League Division One |
| 13 | Sat 13 Sep | 11-2 v PenrithPenrith 2-1 Guisborough Town | Northern League Division One |
| 14 | Wed 17 Sep | 12-1 v Whitley BayGuisborough Town 2-1 Whitley Bay | Northern League Division One |
| 15 | Sat 20 Sep | 12-1 v West Auckland TownGuisborough Town 2-1 West Auckland Town | Northern League Division One |
| 16 | Sat 27 Sep | 12-0 v Newcastle BenfieldGuisborough Town 2-0 Newcastle Benfield | Northern League Division One |
| 17 | Sat 4 Oct | 13-0 v Marske UnitedMarske United 0-3 Guisborough Town | Northern League Division One |
| 18 | Sat 11 Oct | 13-1 v Horden Community WelfareGuisborough Town 3-1 Horden Community Welfare | Northern League Division One |
| 19 | Sat 18 Oct | 13-3 v Newcastle Blue StarNewcastle Blue Star 3-3 Guisborough Town | Northern League Division One |
| 20 | Sat 25 Oct | 11-0 v Crook TownCrook Town 0-1 Guisborough Town | Northern League Division One |
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