| 1 | Wed 29 Jul | 120-2 v Retford UnitedRetford United 2-0 Pickering Town | Northern Counties East League Premier Division |
| 2 | Tue 4 Aug | 172-3 v Worsbrough Bridge AthleticPickering Town 2-3 Worsbrough Bridge Athletic | Northern Counties East League Premier Division |
| 3 | Fri 28 Aug | 164-0 v Keighley TownPickering Town 4-0 Keighley Town | Northern Counties East League Premier Division |
| 4 | Fri 11 Sep | 163-2 v Grangetown Boys ClubPickering Town 3-2 Grangetown Boys Club | FA Vase Second Qualifying Round |
| 5 | Sat 3 Oct | 162-1 v HandsworthPickering Town 2-1 Handsworth | Northern Counties East League Premier Division |
| 6 | Tue 6 Oct | 163-1 v Dearne & DistrictPickering Town 3-1 Dearne & District | Northern Counties East League Cup Second Round |
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