| 1 | Wed 30 Jul | 12 1-0 v Boro RangersGuisborough Town 1-0 Boro Rangers | Northern League Division One |
| 2 | Sat 2 Aug | 162-2 v Consett AFCGuisborough Town 2-2 Consett AFC | Emirates FA Cup Extra Preliminary Round |
| 3 | Tue 5 Aug | 9 2-0 v Consett AFCConsett AFC 0-2 Guisborough Town | Emirates FA Cup Extra Preliminary Round Replay |
| 4 | Sat 9 Aug | 91-1 v West Auckland TownWest Auckland Town 1-1 Guisborough Town | Northern League Division One |
| 5 | Wed 13 Aug | 175-0 v Birtley TownGuisborough Town 5-0 Birtley Town | Northern League Division One |
| 6 | Sat 16 Aug | 150-0 v Redcar AthleticGuisborough Town 0-0 Redcar Athletic | Emirates FA Cup Preliminary Round |
| 7 | Wed 20 Aug | 90-1 v Redcar AthleticRedcar Athletic 1-0 Guisborough Town | Emirates FA Cup Preliminary Round Replay |
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