| 1 | Sat 25 Jul | 110-3 v Bottesford TownBottesford Town 3-0 Pickering Town | Northern Counties East League Premier Division |
| 2 | Wed 29 Jul | 20-2 v Retford UnitedRetford United 2-0 Pickering Town | Northern Counties East League Premier Division |
| 3 | Fri 21 Aug | 153-1 v Golcar UnitedPickering Town 3-1 Golcar United | Northern Counties East League Premier Division |
| 4 | Tue 25 Aug | 150-2 v Albion SportsAlbion Sports 2-0 Pickering Town | Northern Counties East League Premier Division |
| 5 | Tue 8 Sep | 153-2 v Horbury TownPickering Town 3-2 Horbury Town | Northern Counties East League Premier Division |
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