| 1 | Tue 5 Aug | 173-2 v Golcar UnitedPickering Town 3-2 Golcar United | Northern Counties East League Premier Division | 1 |
| 2 | Wed 20 Aug | 152-0 v Easington CollieryEasington Colliery 0-2 Pickering Town | Emirates FA Cup Preliminary Round Replay | 1 |
| 3 | Wed 27 Aug | 94-1 v HandsworthHandsworth 1-4 Pickering Town | Northern Counties East League Premier Division | 2 |
| 4 | Wed 3 Sep | 93-2 v Eccleshill UnitedEccleshill United 2-3 Pickering Town | Northern Counties East League Premier Division | 1 |
| 5 | Tue 9 Sep | 92-3 v Albion SportsAlbion Sports 3-2 Pickering Town | Northern Counties East League Premier Division | 2 |
| 6 | Tue 16 Sep | 9 4-4 v Horbury TownPickering Town 4-4 Horbury Town | Northern Counties East League Premier Division | 3 |
| 7 | Sat 27 Sep | 9 3-3 v Knaresborough TownPickering Town 3-3 Knaresborough Town | Northern Counties East League Premier Division | 1 |
| 8 | Tue 30 Sep | 9 2-0 v Beverley TownPickering Town 2-0 Beverley Town | Northern Counties East League Premier Division | 1 |
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