| 1 | Fri 21 Aug | 173-1 v Golcar UnitedPickering Town 3-1 Golcar United | Northern Counties East League Premier Division |
| 2 | Tue 25 Aug | 170-2 v Albion SportsAlbion Sports 2-0 Pickering Town | Northern Counties East League Premier Division |
| 3 | Fri 28 Aug | 174-0 v Keighley TownPickering Town 4-0 Keighley Town | Northern Counties East League Premier Division |
| 4 | Tue 8 Sep | 173-2 v Horbury TownPickering Town 3-2 Horbury Town | Northern Counties East League Premier Division |
| 5 | Tue 15 Sep | 173-0 v Tadcaster AlbionTadcaster Albion 0-3 Pickering Town | Northern Counties East League Premier Division |
| 6 | Sat 26 Sep | 172-1 v Retford FCPickering Town 2-1 Retford FC | Northern Counties East League Premier Division |
| 7 | Tue 29 Sep | 170-4 v Barton TownBarton Town 4-0 Pickering Town | Northern Counties East League Premier Division |
| 8 | Sat 3 Oct | 172-1 v HandsworthPickering Town 2-1 Handsworth | Northern Counties East League Premier Division |
| 9 | Tue 6 Oct | 93-1 v Dearne & DistrictPickering Town 3-1 Dearne & District | Northern Counties East League Cup Second Round |
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