| 1 | Tue 11 Nov | 82-3 v Scarborough AthleticScarborough Athletic 3-2 Guisborough Town | North Riding Senior Cup |
| 2 | Sat 15 Nov | 154-1 v Easington CollieryGuisborough Town 4-1 Easington Colliery | Northern League Division One |
| 3 | Sat 13 Dec | 152-0 v Kendal TownKendal Town 0-2 Guisborough Town | Northern League Division One |
| 4 | Wed 17 Dec | 123-2 v West Allotment CelticGuisborough Town 3-2 West Allotment Celtic | Northern League Division One |
| 5 | Sat 20 Dec | 163-0 v North ShieldsNorth Shields 0-3 Guisborough Town | Northern League Division One |
| 6 | Fri 26 Dec | 72-1 v Northallerton TownGuisborough Town 2-1 Northallerton Town | Northern League Division One |
| 7 | Tue 20 Jan | 151-3 v Birtley TownBirtley Town 3-1 Guisborough Town | Northern League Division One |
| 8 | Wed 28 Jan | 163-2 v North ShieldsGuisborough Town 3-2 North Shields | Northern League Division One |
| 9 | Sat 21 Feb | 151-0 v Marske UnitedGuisborough Town 1-0 Marske United | Northern League Division One |
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