| 1 | Sat 25 Jul | 60-3 v Bottesford TownBottesford Town 3-0 Pickering Town | Northern Counties East League Premier Division |
| 2 | Sat 8 Aug | 140-4 v Crook TownCrook Town 4-0 Pickering Town | Emirates FA Cup Extra Preliminary Round |
| 3 | Sat 15 Aug | 53-1 v Alnwick TownPickering Town 3-1 Alnwick Town | FA Vase First Qualifying Round |
| 4 | Fri 21 Aug | 23-1 v Golcar UnitedPickering Town 3-1 Golcar United | Northern Counties East League Premier Division |
| 5 | Tue 25 Aug | 60-2 v Albion SportsAlbion Sports 2-0 Pickering Town | Northern Counties East League Premier Division |
| 6 | Fri 28 Aug | 64-0 v Keighley TownPickering Town 4-0 Keighley Town | Northern Counties East League Premier Division |
| 7 | Tue 8 Sep | 63-2 v Horbury TownPickering Town 3-2 Horbury Town | Northern Counties East League Premier Division |
| 8 | Fri 11 Sep | 23-2 v Grangetown Boys ClubPickering Town 3-2 Grangetown Boys Club | FA Vase Second Qualifying Round |
| 9 | Tue 15 Sep | 23-0 v Tadcaster AlbionTadcaster Albion 0-3 Pickering Town | Northern Counties East League Premier Division |
| 10 | Sat 19 Sep | 22-2 v Penistone ChurchPenistone Church 2-2 Pickering Town | Northern Counties East League Premier Division |
| 11 | Sat 26 Sep | 22-1 v Retford FCPickering Town 2-1 Retford FC | Northern Counties East League Premier Division |
| 12 | Tue 29 Sep | 20-4 v Barton TownBarton Town 4-0 Pickering Town | Northern Counties East League Premier Division |
| 13 | Sat 3 Oct | 102-1 v HandsworthPickering Town 2-1 Handsworth | Northern Counties East League Premier Division |
| 14 | Tue 6 Oct | 123-1 v Dearne & DistrictPickering Town 3-1 Dearne & District | Northern Counties East League Cup Second Round |
| 15 | Tue 13 Oct | 91-1 v Dearne & DistrictPickering Town 1-1 Dearne & District | Northern Counties East League Premier Division |
| 16 | Sat 17 Oct | 21-1 v ParkgateParkgate 1-1 Pickering Town | Northern Counties East League Premier Division |
| 17 | Sat 24 Oct | 20-3 v ThackleyPickering Town 0-3 Thackley | Northern Counties East League Premier Division |
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