| 1 | Tue 12 Aug | 171-1 v Campion AFCCampion AFC 1-1 Pickering Town | Northern Counties East League Premier Division |
| 2 | Fri 15 Aug | 170-0 v Easington CollieryPickering Town 0-0 Easington Colliery | Emirates FA Cup Preliminary Round |
| 3 | Wed 20 Aug | 182-0 v Easington CollieryEasington Colliery 0-2 Pickering Town | Emirates FA Cup Preliminary Round Replay |
| 4 | Fri 22 Aug | 32-0 v Horden Community WelfarePickering Town 2-0 Horden Community Welfare | Isuzu FA Vase First Qualifying Round |
| 5 | Wed 3 Sep | 153-2 v Eccleshill UnitedEccleshill United 2-3 Pickering Town | Northern Counties East League Premier Division |
| 6 | Fri 5 Sep | 162-1 v Wombwell TownPickering Town 2-1 Wombwell Town | Northern Counties East League Premier Division |
| 7 | Tue 30 Sep | 172-0 v Beverley TownPickering Town 2-0 Beverley Town | Northern Counties East League Premier Division |
| 8 | Wed 8 Oct | 32-1 v Penistone ChurchPenistone Church 1-2 Pickering Town | Northern Counties East League Cup Second Round |
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