| 1 | Wed 30 Jul | 14 1-0 v Boro RangersGuisborough Town 1-0 Boro Rangers | Northern League Division One |
| 2 | Tue 5 Aug | 22-0 v Consett AFCConsett AFC 0-2 Guisborough Town | Emirates FA Cup Extra Preliminary Round Replay |
| 3 | Sat 9 Aug | 21-1 v West Auckland TownWest Auckland Town 1-1 Guisborough Town | Northern League Division One |
| 4 | Wed 13 Aug | 155-0 v Birtley TownGuisborough Town 5-0 Birtley Town | Northern League Division One |
| 5 | Sat 16 Aug | 20-0 v Redcar AthleticGuisborough Town 0-0 Redcar Athletic | Emirates FA Cup Preliminary Round |
| 6 | Wed 20 Aug | 20-1 v Redcar AthleticRedcar Athletic 1-0 Guisborough Town | Emirates FA Cup Preliminary Round Replay |
| 7 | Sat 4 Oct | 33-0 v Marske UnitedMarske United 0-3 Guisborough Town | Northern League Division One |
| 8 | Sat 11 Oct | 123-1 v Horden Community WelfareGuisborough Town 3-1 Horden Community Welfare | Northern League Division One |
| 9 | Sat 18 Oct | 2 3-3 v Newcastle Blue StarNewcastle Blue Star 3-3 Guisborough Town | Northern League Division One |
| 10 | Sat 8 Nov | 24-3 v ShildonGuisborough Town 4-3 Shildon | Northern League Division One |
| 11 | Sat 15 Nov | 24-1 v Easington CollieryGuisborough Town 4-1 Easington Colliery | Northern League Division One |
| 12 | Sat 22 Nov | 24-0 v Boro RangersBoro Rangers 0-4 Guisborough Town | Northern League Division One |
| 13 | Sat 13 Dec | 22-0 v Kendal TownKendal Town 0-2 Guisborough Town | Northern League Division One |
| 14 | Sat 20 Dec | 2 3-0 v North ShieldsNorth Shields 0-3 Guisborough Town | Northern League Division One |
| 15 | Fri 26 Dec | 22-1 v Northallerton TownGuisborough Town 2-1 Northallerton Town | Northern League Division One |
| 16 | Sat 17 Jan | 22-0 v Whitley BayWhitley Bay 0-2 Guisborough Town | Northern League Division One |
| 17 | Wed 28 Jan | 23-2 v North ShieldsGuisborough Town 3-2 North Shields | Northern League Division One |
| 18 | Sat 21 Feb | 21-0 v Marske UnitedGuisborough Town 1-0 Marske United | Northern League Division One |
| 19 | Wed 4 Mar | 23-1 v PenrithGuisborough Town 3-1 Penrith | Northern League Division One |
| 20 | Sat 7 Mar | 23-1 v Horden Community WelfareHorden Community Welfare 1-3 Guisborough Town | Northern League Division One |
| 21 | Wed 11 Mar | 121-1 v Marske UnitedGuisborough Town 1-1 Marske United | Brooks Mileson Memorial League Cup Second Round |
| 22 | Sat 14 Mar | 22-1 v Newcastle Blue StarGuisborough Town 2-1 Newcastle Blue Star | Northern League Division One |
| 23 | Tue 17 Mar | 2 1-1 v ThornabyThornaby 1-1 Guisborough Town | Northern League Division One |
| 24 | Sat 21 Mar | 124-1 v Crook TownGuisborough Town 4-1 Crook Town | Northern League Division One |
| 25 | Wed 25 Mar | 162-0 v WhickhamWhickham 0-2 Guisborough Town | Northern League Division One |
| 26 | Sat 28 Mar | 21-0 v Newcastle BenfieldNewcastle Benfield 0-1 Guisborough Town | Northern League Division One |
| 27 | Sat 4 Apr | 22-0 v Northallerton TownNorthallerton Town 0-2 Guisborough Town | Northern League Division One |
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