| 1 | Wed 29 Jul | 60-2 v Retford UnitedRetford United 2-0 Pickering Town | Northern Counties East League Premier Division |
| 2 | Tue 4 Aug | 22-3 v Worsbrough Bridge AthleticPickering Town 2-3 Worsbrough Bridge Athletic | Northern Counties East League Premier Division |
| 3 | Sat 8 Aug | 20-4 v Crook TownCrook Town 4-0 Pickering Town | Emirates FA Cup Extra Preliminary Round |
| 4 | Tue 11 Aug | 21-4 v Rossington MainRossington Main 4-1 Pickering Town | Northern Counties East League Premier Division |
| 5 | Sat 15 Aug | 23-1 v Alnwick TownPickering Town 3-1 Alnwick Town | FA Vase First Qualifying Round |
| 6 | Fri 21 Aug | 183-1 v Golcar UnitedPickering Town 3-1 Golcar United | Northern Counties East League Premier Division |
| 7 | Tue 25 Aug | 20-2 v Albion SportsAlbion Sports 2-0 Pickering Town | Northern Counties East League Premier Division |
| 8 | Fri 28 Aug | 24-0 v Keighley TownPickering Town 4-0 Keighley Town | Northern Counties East League Premier Division |
| 9 | Tue 8 Sep | 23-2 v Horbury TownPickering Town 3-2 Horbury Town | Northern Counties East League Premier Division |
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