| 1 | Wed 23 Oct | 151-3 v North ShieldsNorth Shields 3-1 Guisborough Town | Northern League Division One |
| 2 | Sat 26 Oct | 173-0 v Newcastle BenfieldGuisborough Town 3-0 Newcastle Benfield | Northern League Division One |
| 3 | Tue 29 Oct | 74-0 v WhickhamWhickham 0-4 Guisborough Town | Northern League Division One |
| 4 | Wed 4 Dec | 71-1 v Crook TownCrook Town 1-1 Guisborough Town | Northern League Division One |
| 5 | Fri 13 Dec | 71-1 v Birtley TownBirtley Town 1-1 Guisborough Town | Northern League Division One |
| 6 | Sat 21 Dec | 72-0 v PenrithPenrith 0-2 Guisborough Town | Northern League Division One |
| 7 | Sat 28 Dec | 144-1 v Tow Law TownGuisborough Town 4-1 Tow Law Town | Northern League Division One |
| 8 | Sat 4 Jan | 144-0 v Boro RangersBoro Rangers 0-4 Guisborough Town | Northern League Division One |
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