| 1 | Sat 2 Aug | 82-2 v Consett AFCGuisborough Town 2-2 Consett AFC | Emirates FA Cup Extra Preliminary Round |
| 2 | Sat 16 Aug | 170-0 v Redcar AthleticGuisborough Town 0-0 Redcar Athletic | Emirates FA Cup Preliminary Round |
| 3 | Wed 20 Aug | 140-1 v Redcar AthleticRedcar Athletic 1-0 Guisborough Town | Emirates FA Cup Preliminary Round Replay |
| 4 | Tue 26 Aug | 160-1 v West Allotment CelticWest Allotment Celtic 1-0 Guisborough Town | Northern League Division One |
| 5 | Sat 30 Aug | 71-0 v WhickhamGuisborough Town 1-0 Whickham | Northern League Division One |
| 6 | Sat 6 Sep | 73-1 v Kendal TownGuisborough Town 3-1 Kendal Town | Northern League Division One |
| 7 | Wed 10 Sep | 72-0 v ThornabyGuisborough Town 2-0 Thornaby | Northern League Division One |
| 8 | Sat 13 Sep | 71-2 v PenrithPenrith 2-1 Guisborough Town | Northern League Division One |
| 9 | Wed 17 Sep | 72-1 v Whitley BayGuisborough Town 2-1 Whitley Bay | Northern League Division One |
| 10 | Sat 20 Sep | 72-1 v West Auckland TownGuisborough Town 2-1 West Auckland Town | Northern League Division One |
| 11 | Sat 27 Sep | 72-0 v Newcastle BenfieldGuisborough Town 2-0 Newcastle Benfield | Northern League Division One |
| 12 | Tue 11 Nov | 72-3 v Scarborough AthleticScarborough Athletic 3-2 Guisborough Town | North Riding Senior Cup |
| 13 | Sat 15 Nov | 74-1 v Easington CollieryGuisborough Town 4-1 Easington Colliery | Northern League Division One |
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