| 1 | Fri 5 Sep | 32-1 v Wombwell TownPickering Town 2-1 Wombwell Town | Northern Counties East League Premier Division |
| 2 | Tue 9 Sep | 22-3 v Albion SportsAlbion Sports 3-2 Pickering Town | Northern Counties East League Premier Division |
| 3 | Sat 13 Sep | 120-2 v Runcorn LinnetsPickering Town 0-2 Runcorn Linnets | Emirates FA Cup Second Qualifying Round |
| 4 | Tue 16 Sep | 114-4 v Horbury TownPickering Town 4-4 Horbury Town | Northern Counties East League Premier Division |
| 5 | Sat 20 Sep | 70-1 v Yarm & EaglescliffePickering Town 0-1 Yarm & Eaglescliffe | Isuzu FA Vase Second Qualifying Round |
| 6 | Sat 27 Sep | 33-3 v Knaresborough TownPickering Town 3-3 Knaresborough Town | Northern Counties East League Premier Division |
| 7 | Tue 30 Sep | 3 2-0 v Beverley TownPickering Town 2-0 Beverley Town | Northern Counties East League Premier Division |
| 8 | Sat 4 Oct | 32-3 v ThackleyPickering Town 2-3 Thackley | Northern Counties East League Premier Division |
| 9 | Wed 8 Oct | 152-1 v Penistone ChurchPenistone Church 1-2 Pickering Town | Northern Counties East League Cup Second Round |
| 10 | Sat 11 Oct | 11 3-0 v Barton TownBarton Town 0-3 Pickering Town | Northern Counties East League Premier Division |
| 11 | Tue 14 Oct | 32-0 v SheffieldPickering Town 2-0 Sheffield | Northern Counties East League Premier Division |
| 12 | Sat 18 Oct | 31-5 v Bottesford TownBottesford Town 5-1 Pickering Town | Northern Counties East League Premier Division |
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