| 1 | Sat 26 Jul | 52-1 v Easington CollieryEasington Colliery 1-2 Guisborough Town | Northern League Division One |
| 2 | Wed 30 Jul | 51-0 v Boro RangersGuisborough Town 1-0 Boro Rangers | Northern League Division One |
| 3 | Sat 2 Aug | 52-2 v Consett AFCGuisborough Town 2-2 Consett AFC | Emirates FA Cup Extra Preliminary Round |
| 4 | Sat 9 Aug | 141-1 v West Auckland TownWest Auckland Town 1-1 Guisborough Town | Northern League Division One |
| 5 | Wed 13 Aug | 55-0 v Birtley TownGuisborough Town 5-0 Birtley Town | Northern League Division One |
| 6 | Sat 16 Aug | 50-0 v Redcar AthleticGuisborough Town 0-0 Redcar Athletic | Emirates FA Cup Preliminary Round |
| 7 | Wed 20 Aug | 50-1 v Redcar AthleticRedcar Athletic 1-0 Guisborough Town | Emirates FA Cup Preliminary Round Replay |
| 8 | Sat 30 Aug | 51-0 v WhickhamGuisborough Town 1-0 Whickham | Northern League Division One |
| 9 | Sat 6 Sep | 53-1 v Kendal TownGuisborough Town 3-1 Kendal Town | Northern League Division One |
| 10 | Wed 10 Sep | 52-0 v ThornabyGuisborough Town 2-0 Thornaby | Northern League Division One |
| 11 | Sat 13 Sep | 5 1-2 v PenrithPenrith 2-1 Guisborough Town | Northern League Division One |
| 12 | Wed 17 Sep | 52-1 v Whitley BayGuisborough Town 2-1 Whitley Bay | Northern League Division One |
| 13 | Sat 20 Sep | 52-1 v West Auckland TownGuisborough Town 2-1 West Auckland Town | Northern League Division One |
| 14 | Sat 27 Sep | 52-0 v Newcastle BenfieldGuisborough Town 2-0 Newcastle Benfield | Northern League Division One |
| 15 | Sat 4 Oct | 53-0 v Marske UnitedMarske United 0-3 Guisborough Town | Northern League Division One |
| 16 | Sat 11 Oct | 53-1 v Horden Community WelfareGuisborough Town 3-1 Horden Community Welfare | Northern League Division One |
| 17 | Sat 18 Oct | 53-3 v Newcastle Blue StarNewcastle Blue Star 3-3 Guisborough Town | Northern League Division One |
| 18 | Sat 25 Oct | 51-0 v Crook TownCrook Town 0-1 Guisborough Town | Northern League Division One |
| 19 | Sat 1 Nov | 52-2 v Carlisle CityGuisborough Town 2-2 Carlisle City | Northern League Division One |
| 20 | Sat 8 Nov | 54-3 v ShildonGuisborough Town 4-3 Shildon | Northern League Division One |
| 21 | Tue 11 Nov | 52-3 v Scarborough AthleticScarborough Athletic 3-2 Guisborough Town | North Riding Senior Cup |
| 22 | Sat 15 Nov | 54-1 v Easington CollieryGuisborough Town 4-1 Easington Colliery | Northern League Division One |
| 23 | Sat 22 Nov | 54-0 v Boro RangersBoro Rangers 0-4 Guisborough Town | Northern League Division One |
| 24 | Sat 13 Dec | 52-0 v Kendal TownKendal Town 0-2 Guisborough Town | Northern League Division One |
| 25 | Sat 20 Dec | 53-0 v North ShieldsNorth Shields 0-3 Guisborough Town | Northern League Division One |
| 26 | Fri 26 Dec | 52-1 v Northallerton TownGuisborough Town 2-1 Northallerton Town | Northern League Division One |
| 27 | Sat 17 Jan | 52-0 v Whitley BayWhitley Bay 0-2 Guisborough Town | Northern League Division One |
| 28 | Wed 28 Jan | 53-2 v North ShieldsGuisborough Town 3-2 North Shields | Northern League Division One |
| 29 | Sat 21 Feb | 5 1-0 v Marske UnitedGuisborough Town 1-0 Marske United | Northern League Division One |
| 30 | Wed 4 Mar | 53-1 v PenrithGuisborough Town 3-1 Penrith | Northern League Division One |
| 31 | Sat 7 Mar | 53-1 v Horden Community WelfareHorden Community Welfare 1-3 Guisborough Town | Northern League Division One |
| 32 | Sat 14 Mar | 52-1 v Newcastle Blue StarGuisborough Town 2-1 Newcastle Blue Star | Northern League Division One |
| 33 | Tue 17 Mar | 51-1 v ThornabyThornaby 1-1 Guisborough Town | Northern League Division One |
| 34 | Sat 21 Mar | 54-1 v Crook TownGuisborough Town 4-1 Crook Town | Northern League Division One |
| 35 | Wed 25 Mar | 52-0 v WhickhamWhickham 0-2 Guisborough Town | Northern League Division One |
| 36 | Sat 28 Mar | 51-0 v Newcastle BenfieldNewcastle Benfield 0-1 Guisborough Town | Northern League Division One |
| 37 | Sat 4 Apr | 52-0 v Northallerton TownNorthallerton Town 0-2 Guisborough Town | Northern League Division One |
| 38 | Sat 11 Apr | 54-1 v Carlisle CityCarlisle City 1-4 Guisborough Town | Northern League Division One |
| 39 | Sat 18 Apr | 55-2 v ShildonShildon 2-5 Guisborough Town | Northern League Division One |
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