| 1 | Fri 21 Aug | 123-1 v Golcar UnitedPickering Town 3-1 Golcar United | Northern Counties East League Premier Division |
| 2 | Fri 28 Aug | 124-0 v Keighley TownPickering Town 4-0 Keighley Town | Northern Counties East League Premier Division |
| 3 | Tue 8 Sep | 123-2 v Horbury TownPickering Town 3-2 Horbury Town | Northern Counties East League Premier Division |
| 4 | Fri 11 Sep | 63-2 v Grangetown Boys ClubPickering Town 3-2 Grangetown Boys Club | FA Vase Second Qualifying Round |
| 5 | Tue 15 Sep | 123-0 v Tadcaster AlbionTadcaster Albion 0-3 Pickering Town | Northern Counties East League Premier Division |
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