| 1 | Sat 21 Feb | 71-0 v Marske UnitedGuisborough Town 1-0 Marske United | Northern League Division One |
| 2 | Wed 4 Mar | 83-1 v PenrithGuisborough Town 3-1 Penrith | Northern League Division One |
| 3 | Sat 7 Mar | 73-1 v Horden Community WelfareHorden Community Welfare 1-3 Guisborough Town | Northern League Division One |
| 4 | Wed 11 Mar | 141-1 v Marske UnitedGuisborough Town 1-1 Marske United | Brooks Mileson Memorial League Cup Second Round |
| 5 | Sat 14 Mar | 72-1 v Newcastle Blue StarGuisborough Town 2-1 Newcastle Blue Star | Northern League Division One |
| 6 | Tue 17 Mar | 141-1 v ThornabyThornaby 1-1 Guisborough Town | Northern League Division One |
| 7 | Sat 21 Mar | 34-1 v Crook TownGuisborough Town 4-1 Crook Town | Northern League Division One |
| 8 | Wed 25 Mar | 72-0 v WhickhamWhickham 0-2 Guisborough Town | Northern League Division One |
| 9 | Sat 28 Mar | 71-0 v Newcastle BenfieldNewcastle Benfield 0-1 Guisborough Town | Northern League Division One |
| 10 | Sat 4 Apr | 72-0 v Northallerton TownNorthallerton Town 0-2 Guisborough Town | Northern League Division One |
| 11 | Sat 11 Apr | 74-1 v Carlisle CityCarlisle City 1-4 Guisborough Town | Northern League Division One |
| 12 | Sat 18 Apr | 75-2 v ShildonShildon 2-5 Guisborough Town | Northern League Division One |
| 13 | Sat 18 Jul | 104-1 v North ShieldsGuisborough Town 4-1 North Shields | Friendly |
| 14 | Sat 8 Aug | 70-1 v ThornabyGuisborough Town 0-1 Thornaby | Emirates FA Cup Extra Preliminary Round |
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