| 1 | Sat 27 Sep | 13-3 v Knaresborough TownPickering Town 3-3 Knaresborough Town | Northern Counties East League Premier Division |
| 2 | Tue 30 Sep | 12-0 v Beverley TownPickering Town 2-0 Beverley Town | Northern Counties East League Premier Division |
| 3 | Sat 4 Oct | 12-3 v ThackleyPickering Town 2-3 Thackley | Northern Counties East League Premier Division |
| 4 | Wed 8 Oct | 12-1 v Penistone ChurchPenistone Church 1-2 Pickering Town | Northern Counties East League Cup Second Round |
| 5 | Sat 11 Oct | 13-0 v Barton TownBarton Town 0-3 Pickering Town | Northern Counties East League Premier Division |
| 6 | Tue 14 Oct | 12-0 v SheffieldPickering Town 2-0 Sheffield | Northern Counties East League Premier Division |
| 7 | Sat 18 Oct | 11-5 v Bottesford TownBottesford Town 5-1 Pickering Town | Northern Counties East League Premier Division |
| 8 | Sat 1 Nov | 12-0 v Penistone ChurchPenistone Church 0-2 Pickering Town | Northern Counties East League Premier Division |
| 9 | Tue 11 Nov | 11-1 v Frickley AthleticFrickley Athletic 1-1 Pickering Town | Northern Counties East League Premier Division |
| 10 | Sat 15 Nov | 11-2 v ParkgatePickering Town 1-2 Parkgate | Northern Counties East League Premier Division |
| 11 | Sat 22 Nov | 10-2 v Golcar UnitedGolcar United 2-0 Pickering Town | Northern Counties East League Premier Division |
| 12 | Tue 25 Nov | 12-3 v LiversedgePickering Town 2-3 Liversedge | Northern Counties East League Cup Third Round |
| 13 | Sat 29 Nov | 10-4 v Campion AFCPickering Town 0-4 Campion AFC | Northern Counties East League Premier Division |
| 14 | Sat 13 Dec | 12-3 v SheffieldSheffield 3-2 Pickering Town | Northern Counties East League Premier Division |
| 15 | Tue 16 Dec | 10-3 v Albion SportsPickering Town 0-3 Albion Sports | Northern Counties East League Premier Division |
| 16 | Sat 20 Dec | 14-1 v HandsworthPickering Town 4-1 Handsworth | Northern Counties East League Premier Division |
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