| 1 | Sat 26 Jul | 11 2-1 v Easington CollieryEasington Colliery 1-2 Guisborough Town | Northern League Division One |
| 2 | Wed 30 Jul | 71-0 v Boro RangersGuisborough Town 1-0 Boro Rangers | Northern League Division One |
| 3 | Sat 2 Aug | 142-2 v Consett AFCGuisborough Town 2-2 Consett AFC | Emirates FA Cup Extra Preliminary Round |
| 4 | Tue 5 Aug | 142-0 v Consett AFCConsett AFC 0-2 Guisborough Town | Emirates FA Cup Extra Preliminary Round Replay |
| 5 | Sat 9 Aug | 121-1 v West Auckland TownWest Auckland Town 1-1 Guisborough Town | Northern League Division One |
| 6 | Wed 13 Aug | 75-0 v Birtley TownGuisborough Town 5-0 Birtley Town | Northern League Division One |
| 7 | Sat 16 Aug | 110-0 v Redcar AthleticGuisborough Town 0-0 Redcar Athletic | Emirates FA Cup Preliminary Round |
| 8 | Wed 20 Aug | 180-1 v Redcar AthleticRedcar Athletic 1-0 Guisborough Town | Emirates FA Cup Preliminary Round Replay |
| 9 | Sat 30 Aug | 111-0 v WhickhamGuisborough Town 1-0 Whickham | Northern League Division One |
| 10 | Wed 10 Sep | 172-0 v ThornabyGuisborough Town 2-0 Thornaby | Northern League Division One |
| 11 | Sat 13 Sep | 101-2 v PenrithPenrith 2-1 Guisborough Town | Northern League Division One |
| 12 | Wed 17 Sep | 112-1 v Whitley BayGuisborough Town 2-1 Whitley Bay | Northern League Division One |
| 13 | Sat 20 Sep | 172-1 v West Auckland TownGuisborough Town 2-1 West Auckland Town | Northern League Division One |
| 14 | Sat 27 Sep | 122-0 v Newcastle BenfieldGuisborough Town 2-0 Newcastle Benfield | Northern League Division One |
| 15 | Sat 4 Oct | 7 3-0 v Marske UnitedMarske United 0-3 Guisborough Town | Northern League Division One |
| 16 | Sat 18 Oct | 153-3 v Newcastle Blue StarNewcastle Blue Star 3-3 Guisborough Town | Northern League Division One |
| 17 | Sat 1 Nov | 82-2 v Carlisle CityGuisborough Town 2-2 Carlisle City | Northern League Division One |
| 18 | Sat 8 Nov | 164-3 v ShildonGuisborough Town 4-3 Shildon | Northern League Division One |
| 19 | Tue 11 Nov | 11 2-3 v Scarborough AthleticScarborough Athletic 3-2 Guisborough Town | North Riding Senior Cup |
| 20 | Sat 15 Nov | 124-1 v Easington CollieryGuisborough Town 4-1 Easington Colliery | Northern League Division One |
| 21 | Sat 22 Nov | 7 4-0 v Boro RangersBoro Rangers 0-4 Guisborough Town | Northern League Division One |
| 22 | Sat 13 Dec | 142-0 v Kendal TownKendal Town 0-2 Guisborough Town | Northern League Division One |
| 23 | Sat 20 Dec | 153-0 v North ShieldsNorth Shields 0-3 Guisborough Town | Northern League Division One |
| 24 | Fri 26 Dec | 102-1 v Northallerton TownGuisborough Town 2-1 Northallerton Town | Northern League Division One |
| 25 | Sat 17 Jan | 102-0 v Whitley BayWhitley Bay 0-2 Guisborough Town | Northern League Division One |
| 26 | Tue 20 Jan | 101-3 v Birtley TownBirtley Town 3-1 Guisborough Town | Northern League Division One |
| 27 | Sat 21 Feb | 121-0 v Marske UnitedGuisborough Town 1-0 Marske United | Northern League Division One |
| 28 | Wed 4 Mar | 11 3-1 v PenrithGuisborough Town 3-1 Penrith | Northern League Division One |
| 29 | Sat 7 Mar | 113-1 v Horden Community WelfareHorden Community Welfare 1-3 Guisborough Town | Northern League Division One |
| 30 | Wed 11 Mar | 161-1 v Marske UnitedGuisborough Town 1-1 Marske United | Brooks Mileson Memorial League Cup Second Round |
| 31 | Sat 14 Mar | 102-1 v Newcastle Blue StarGuisborough Town 2-1 Newcastle Blue Star | Northern League Division One |
| 32 | Tue 17 Mar | 101-1 v ThornabyThornaby 1-1 Guisborough Town | Northern League Division One |
| 33 | Sat 21 Mar | 24-1 v Crook TownGuisborough Town 4-1 Crook Town | Northern League Division One |
| 34 | Wed 25 Mar | 22-0 v WhickhamWhickham 0-2 Guisborough Town | Northern League Division One |
| 35 | Sat 4 Apr | 102-0 v Northallerton TownNorthallerton Town 0-2 Guisborough Town | Northern League Division One |
| 36 | Sat 11 Apr | 24-1 v Carlisle CityCarlisle City 1-4 Guisborough Town | Northern League Division One |
| 37 | Sat 18 Apr | 105-2 v ShildonShildon 2-5 Guisborough Town | Northern League Division One |
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