| 1 | Sat 19 Sep | 112-2 v Penistone ChurchPenistone Church 2-2 Pickering Town | Northern Counties East League Premier Division |
| 2 | Sat 26 Sep | 112-1 v Retford FCPickering Town 2-1 Retford FC | Northern Counties East League Premier Division |
| 3 | Tue 29 Sep | 100-4 v Barton TownBarton Town 4-0 Pickering Town | Northern Counties East League Premier Division |
| 4 | Sat 3 Oct | 7 2-1 v HandsworthPickering Town 2-1 Handsworth | Northern Counties East League Premier Division |
| 5 | Tue 6 Oct | 10 3-1 v Dearne & DistrictPickering Town 3-1 Dearne & District | Northern Counties East League Cup Second Round |
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