| 1 | Fri 22 Aug | 162-0 v Horden Community WelfarePickering Town 2-0 Horden Community Welfare | Isuzu FA Vase First Qualifying Round |
| 2 | Wed 27 Aug | 164-1 v HandsworthHandsworth 1-4 Pickering Town | Northern Counties East League Premier Division |
| 3 | Fri 29 Aug | 165-2 v Redcar AthleticPickering Town 5-2 Redcar Athletic | Emirates FA Cup First Qualifying Round |
| 4 | Wed 3 Sep | 123-2 v Eccleshill UnitedEccleshill United 2-3 Pickering Town | Northern Counties East League Premier Division |
| 5 | Fri 5 Sep | 152-1 v Wombwell TownPickering Town 2-1 Wombwell Town | Northern Counties East League Premier Division |
| 6 | Tue 9 Sep | 172-3 v Albion SportsAlbion Sports 3-2 Pickering Town | Northern Counties East League Premier Division |
| 7 | Tue 30 Sep | 182-0 v Beverley TownPickering Town 2-0 Beverley Town | Northern Counties East League Premier Division |
| 8 | Wed 8 Oct | 22-1 v Penistone ChurchPenistone Church 1-2 Pickering Town | Northern Counties East League Cup Second Round |
| 9 | Sat 11 Oct | 163-0 v Barton TownBarton Town 0-3 Pickering Town | Northern Counties East League Premier Division |
| 10 | Sat 29 Nov | 140-4 v Campion AFCPickering Town 0-4 Campion AFC | Northern Counties East League Premier Division |
| 11 | Sat 13 Dec | 22-3 v SheffieldSheffield 3-2 Pickering Town | Northern Counties East League Premier Division |
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