| 1 | Sat 21 Sep | 142-1 v ShildonGuisborough Town 2-1 Shildon | Isuzu FA Vase Second Qualifying Round |
| 2 | Sat 28 Sep | 33-2 v Whitley BayGuisborough Town 3-2 Whitley Bay | Northern League Division One |
| 3 | Sat 5 Oct | 31-2 v ShildonShildon 2-1 Guisborough Town | Northern League Division One |
| 4 | Wed 9 Oct | 31-1 v Blyth TownGuisborough Town 1-1 Blyth Town | Northern League Division One |
| 5 | Sat 12 Oct | 33-2 v Seaham Red StarGuisborough Town 3-2 Seaham Red Star | Northern League Division One |
| 6 | Sat 19 Oct | 30-1 v Carlisle CityGuisborough Town 0-1 Carlisle City | Isuzu FA Vase First Round |
| 7 | Wed 23 Oct | 31-3 v North ShieldsNorth Shields 3-1 Guisborough Town | Northern League Division One |
| 8 | Sat 26 Oct | 33-0 v Newcastle BenfieldGuisborough Town 3-0 Newcastle Benfield | Northern League Division One |
| 9 | Tue 29 Oct | 3 4-0 v WhickhamWhickham 0-4 Guisborough Town | Northern League Division One |
| 10 | Sat 2 Nov | 31-1 v Marske UnitedMarske United 1-1 Guisborough Town | Northern League Division One |
| 11 | Sat 9 Nov | 33-2 v Kendal TownGuisborough Town 3-2 Kendal Town | Northern League Division One |
| 12 | Sat 16 Nov | 33-2 v WhickhamGuisborough Town 3-2 Whickham | Northern League Division One |
| 13 | Sat 30 Nov | 30-0 v Carlisle CityGuisborough Town 0-0 Carlisle City | Northern League Division One |
| 14 | Fri 13 Dec | 31-1 v Birtley TownBirtley Town 1-1 Guisborough Town | Northern League Division One |
| 15 | Sat 21 Dec | 32-0 v PenrithPenrith 0-2 Guisborough Town | Northern League Division One |
| 16 | Thu 26 Dec | 32-3 v Boro RangersGuisborough Town 2-3 Boro Rangers | Northern League Division One |
| 17 | Sat 28 Dec | 34-1 v Tow Law TownGuisborough Town 4-1 Tow Law Town | Northern League Division One |
| 18 | Sat 4 Jan | 34-0 v Boro RangersBoro Rangers 0-4 Guisborough Town | Northern League Division One |
| 19 | Sat 18 Jan | 30-2 v Redcar AthleticRedcar Athletic 2-0 Guisborough Town | Northern League Division One |
| 20 | Sat 25 Jan | 30-1 v Newcastle Blue StarGuisborough Town 0-1 Newcastle Blue Star | Northern League Division One |
| 21 | Sat 15 Feb | 31-4 v West Auckland TownWest Auckland Town 4-1 Guisborough Town | Northern League Division One |
| 22 | Sat 22 Feb | 30-0 v West Allotment CelticGuisborough Town 0-0 West Allotment Celtic | Northern League Division One |
| 23 | Wed 26 Feb | 31-2 v Northallerton TownGuisborough Town 1-2 Northallerton Town | Northern League Division One |
| 24 | Sat 1 Mar | 33-1 v Blyth TownBlyth Town 1-3 Guisborough Town | Northern League Division One |
| 25 | Sat 8 Mar | 31-1 v Whitley BayWhitley Bay 1-1 Guisborough Town | Northern League Division One |
| 26 | Sat 22 Mar | 30-0 v Seaham Red StarSeaham Red Star 0-0 Guisborough Town | Northern League Division One |
| 27 | Sat 29 Mar | 31-1 v ShildonGuisborough Town 1-1 Shildon | Northern League Division One |
| 28 | Sat 5 Apr | 32-1 v North ShieldsGuisborough Town 2-1 North Shields | Northern League Division One |
| 29 | Sat 12 Apr | 30-1 v Newcastle BenfieldNewcastle Benfield 1-0 Guisborough Town | Northern League Division One |
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