| 1 | Fri 22 Aug | 92-0 v Horden Community WelfarePickering Town 2-0 Horden Community Welfare | Isuzu FA Vase First Qualifying Round |
| 2 | Wed 27 Aug | 114-1 v HandsworthHandsworth 1-4 Pickering Town | Northern Counties East League Premier Division |
| 3 | Sat 27 Sep | 143-3 v Knaresborough TownPickering Town 3-3 Knaresborough Town | Northern Counties East League Premier Division |
| 4 | Tue 30 Sep | 72-0 v Beverley TownPickering Town 2-0 Beverley Town | Northern Counties East League Premier Division |
| 5 | Sat 4 Oct | 72-3 v ThackleyPickering Town 2-3 Thackley | Northern Counties East League Premier Division |
| 6 | Wed 8 Oct | 92-1 v Penistone ChurchPenistone Church 1-2 Pickering Town | Northern Counties East League Cup Second Round |
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