| 1 | Sat 17 Jan | 122-0 v Whitley BayWhitley Bay 0-2 Guisborough Town | Northern League Division One |
| 2 | Tue 20 Jan | 51-3 v Birtley TownBirtley Town 3-1 Guisborough Town | Northern League Division One |
| 3 | Wed 28 Jan | 63-2 v North ShieldsGuisborough Town 3-2 North Shields | Northern League Division One |
| 4 | Sat 21 Feb | 61-0 v Marske UnitedGuisborough Town 1-0 Marske United | Northern League Division One |
| 5 | Wed 4 Mar | 63-1 v PenrithGuisborough Town 3-1 Penrith | Northern League Division One |
| 6 | Sat 7 Mar | 43-1 v Horden Community WelfareHorden Community Welfare 1-3 Guisborough Town | Northern League Division One |
| 7 | Sat 14 Mar | 62-1 v Newcastle Blue StarGuisborough Town 2-1 Newcastle Blue Star | Northern League Division One |
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