| 1 | Sat 11 Oct | 73-1 v Horden Community WelfareGuisborough Town 3-1 Horden Community Welfare | Northern League Division One |
| 2 | Sat 18 Oct | 73-3 v Newcastle Blue StarNewcastle Blue Star 3-3 Guisborough Town | Northern League Division One |
| 3 | Sat 25 Oct | 71-0 v Crook TownCrook Town 0-1 Guisborough Town | Northern League Division One |
| 4 | Sat 1 Nov | 72-2 v Carlisle CityGuisborough Town 2-2 Carlisle City | Northern League Division One |
| 5 | Sat 8 Nov | 74-3 v ShildonGuisborough Town 4-3 Shildon | Northern League Division One |
| 6 | Tue 11 Nov | 102-3 v Scarborough AthleticScarborough Athletic 3-2 Guisborough Town | North Riding Senior Cup |
| 7 | Sat 15 Nov | 84-1 v Easington CollieryGuisborough Town 4-1 Easington Colliery | Northern League Division One |
| 8 | Sat 22 Nov | 104-0 v Boro RangersBoro Rangers 0-4 Guisborough Town | Northern League Division One |
| 9 | Sat 13 Dec | 102-0 v Kendal TownKendal Town 0-2 Guisborough Town | Northern League Division One |
| 10 | Wed 17 Dec | 73-2 v West Allotment CelticGuisborough Town 3-2 West Allotment Celtic | Northern League Division One |
| 11 | Sat 20 Dec | 73-0 v North ShieldsNorth Shields 0-3 Guisborough Town | Northern League Division One |
| 12 | Fri 26 Dec | 112-1 v Northallerton TownGuisborough Town 2-1 Northallerton Town | Northern League Division One |
| 13 | Sat 17 Jan | 72-0 v Whitley BayWhitley Bay 0-2 Guisborough Town | Northern League Division One |
| 14 | Tue 20 Jan | 71-3 v Birtley TownBirtley Town 3-1 Guisborough Town | Northern League Division One |
| 15 | Wed 28 Jan | 73-2 v North ShieldsGuisborough Town 3-2 North Shields | Northern League Division One |
| 16 | Sat 21 Feb | 71-0 v Marske UnitedGuisborough Town 1-0 Marske United | Northern League Division One |
| 17 | Wed 4 Mar | 83-1 v PenrithGuisborough Town 3-1 Penrith | Northern League Division One |
| 18 | Sat 7 Mar | 73-1 v Horden Community WelfareHorden Community Welfare 1-3 Guisborough Town | Northern League Division One |
| 19 | Wed 11 Mar | 141-1 v Marske UnitedGuisborough Town 1-1 Marske United | Brooks Mileson Memorial League Cup Second Round |
| 20 | Sat 14 Mar | 72-1 v Newcastle Blue StarGuisborough Town 2-1 Newcastle Blue Star | Northern League Division One |
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