| 1 | Sat 27 Jul | 13-1 v Northallerton TownNorthallerton Town 1-3 Guisborough Town | Northern League Division One |
| 2 | Tue 30 Jul | 10-1 v Kendal TownKendal Town 1-0 Guisborough Town | Northern League Division One |
| 3 | Sat 3 Aug | 1 2-2 v Kendal TownKendal Town 2-2 Guisborough Town | Emirates FA Cup Extra Preliminary Round |
| 4 | Wed 7 Aug | 11-2 v Kendal TownGuisborough Town 1-2 Kendal Town | Emirates FA Cup Extra Preliminary Round Replay |
| 5 | Sat 10 Aug | 12-0 v Newcastle Blue StarNewcastle Blue Star 0-2 Guisborough Town | Northern League Division One |
| 6 | Wed 14 Aug | 10-3 v Crook TownGuisborough Town 0-3 Crook Town | Northern League Division One |
| 7 | Tue 20 Aug | 11-1 v Carlisle CityCarlisle City 1-1 Guisborough Town | Northern League Division One |
| 8 | Sat 24 Aug | 11-1 v Redcar AthleticGuisborough Town 1-1 Redcar Athletic | Northern League Division One |
| 9 | Wed 28 Aug | 15-1 v Birtley TownGuisborough Town 5-1 Birtley Town | Northern League Division One |
| 10 | Wed 4 Sep | 12-1 v PenrithGuisborough Town 2-1 Penrith | Northern League Division One |
| 11 | Sat 7 Sep | 1 0-4 v West Auckland TownGuisborough Town 0-4 West Auckland Town | Northern League Division One |
| 12 | Sat 14 Sep | 10-0 v West Allotment CelticWest Allotment Celtic 0-0 Guisborough Town | Northern League Division One |
| 13 | Tue 17 Sep | 12-2 v Tow Law TownTow Law Town 2-2 Guisborough Town | Northern League Division One |
| 14 | Sat 21 Sep | 12-1 v ShildonGuisborough Town 2-1 Shildon | Isuzu FA Vase Second Qualifying Round |
| 15 | Sat 28 Sep | 13-2 v Whitley BayGuisborough Town 3-2 Whitley Bay | Northern League Division One |
| 16 | Sat 5 Oct | 11-2 v ShildonShildon 2-1 Guisborough Town | Northern League Division One |
| 17 | Wed 9 Oct | 11-1 v Blyth TownGuisborough Town 1-1 Blyth Town | Northern League Division One |
| 18 | Sat 12 Oct | 13-2 v Seaham Red StarGuisborough Town 3-2 Seaham Red Star | Northern League Division One |
| 19 | Sat 19 Oct | 10-1 v Carlisle CityGuisborough Town 0-1 Carlisle City | Isuzu FA Vase First Round |
| 20 | Wed 23 Oct | 11-3 v North ShieldsNorth Shields 3-1 Guisborough Town | Northern League Division One |
| 21 | Sat 26 Oct | 13-0 v Newcastle BenfieldGuisborough Town 3-0 Newcastle Benfield | Northern League Division One |
| 22 | Tue 29 Oct | 14-0 v WhickhamWhickham 0-4 Guisborough Town | Northern League Division One |
| 23 | Sat 2 Nov | 11-1 v Marske UnitedMarske United 1-1 Guisborough Town | Northern League Division One |
| 24 | Sat 9 Nov | 13-2 v Kendal TownGuisborough Town 3-2 Kendal Town | Northern League Division One |
| 25 | Sat 16 Nov | 13-2 v WhickhamGuisborough Town 3-2 Whickham | Northern League Division One |
| 26 | Sat 30 Nov | 10-0 v Carlisle CityGuisborough Town 0-0 Carlisle City | Northern League Division One |
| 27 | Wed 4 Dec | 11-1 v Crook TownCrook Town 1-1 Guisborough Town | Northern League Division One |
| 28 | Fri 13 Dec | 11-1 v Birtley TownBirtley Town 1-1 Guisborough Town | Northern League Division One |
| 29 | Sat 21 Dec | 12-0 v PenrithPenrith 0-2 Guisborough Town | Northern League Division One |
| 30 | Thu 26 Dec | 12-3 v Boro RangersGuisborough Town 2-3 Boro Rangers | Northern League Division One |
| 31 | Sat 28 Dec | 1 4-1 v Tow Law TownGuisborough Town 4-1 Tow Law Town | Northern League Division One |
| 32 | Sat 4 Jan | 14-0 v Boro RangersBoro Rangers 0-4 Guisborough Town | Northern League Division One |
| 33 | Sat 18 Jan | 10-2 v Redcar AthleticRedcar Athletic 2-0 Guisborough Town | Northern League Division One |
| 34 | Sat 25 Jan | 10-1 v Newcastle Blue StarGuisborough Town 0-1 Newcastle Blue Star | Northern League Division One |
| 35 | Sat 15 Feb | 11-4 v West Auckland TownWest Auckland Town 4-1 Guisborough Town | Northern League Division One |
| 36 | Sat 22 Feb | 10-0 v West Allotment CelticGuisborough Town 0-0 West Allotment Celtic | Northern League Division One |
| 37 | Wed 26 Feb | 11-2 v Northallerton TownGuisborough Town 1-2 Northallerton Town | Northern League Division One |
| 38 | Sat 1 Mar | 13-1 v Blyth TownBlyth Town 1-3 Guisborough Town | Northern League Division One |
| 39 | Sat 8 Mar | 11-1 v Whitley BayWhitley Bay 1-1 Guisborough Town | Northern League Division One |
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