| 1 | Sat 25 Jul | 40-3 v Bottesford TownBottesford Town 3-0 Pickering Town | Northern Counties East League Premier Division |
| 2 | Tue 4 Aug | 42-3 v Worsbrough Bridge AthleticPickering Town 2-3 Worsbrough Bridge Athletic | Northern Counties East League Premier Division |
| 3 | Sat 8 Aug | 40-4 v Crook TownCrook Town 4-0 Pickering Town | Emirates FA Cup Extra Preliminary Round |
| 4 | Tue 11 Aug | 41-4 v Rossington MainRossington Main 4-1 Pickering Town | Northern Counties East League Premier Division |
| 5 | Sat 15 Aug | 43-1 v Alnwick TownPickering Town 3-1 Alnwick Town | FA Vase First Qualifying Round |
| 6 | Fri 21 Aug | 43-1 v Golcar UnitedPickering Town 3-1 Golcar United | Northern Counties East League Premier Division |
| 7 | Tue 25 Aug | 40-2 v Albion SportsAlbion Sports 2-0 Pickering Town | Northern Counties East League Premier Division |
| 8 | Fri 28 Aug | 44-0 v Keighley TownPickering Town 4-0 Keighley Town | Northern Counties East League Premier Division |
| 9 | Tue 15 Sep | 43-0 v Tadcaster AlbionTadcaster Albion 0-3 Pickering Town | Northern Counties East League Premier Division |
| 10 | Sat 19 Sep | 42-2 v Penistone ChurchPenistone Church 2-2 Pickering Town | Northern Counties East League Premier Division |
| 11 | Sat 26 Sep | 42-1 v Retford FCPickering Town 2-1 Retford FC | Northern Counties East League Premier Division |
| 12 | Tue 29 Sep | 4 0-4 v Barton TownBarton Town 4-0 Pickering Town | Northern Counties East League Premier Division |
| 13 | Sat 3 Oct | 32-1 v HandsworthPickering Town 2-1 Handsworth | Northern Counties East League Premier Division |
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