| 1 | Sat 25 Jul | 10-3 v Bottesford TownBottesford Town 3-0 Pickering Town | Northern Counties East League Premier Division |
| 2 | Wed 29 Jul | 10-2 v Retford UnitedRetford United 2-0 Pickering Town | Northern Counties East League Premier Division |
| 3 | Tue 4 Aug | 12-3 v Worsbrough Bridge AthleticPickering Town 2-3 Worsbrough Bridge Athletic | Northern Counties East League Premier Division |
| 4 | Sat 8 Aug | 10-4 v Crook TownCrook Town 4-0 Pickering Town | Emirates FA Cup Extra Preliminary Round |
| 5 | Tue 11 Aug | 11-4 v Rossington MainRossington Main 4-1 Pickering Town | Northern Counties East League Premier Division |
| 6 | Sat 15 Aug | 13-1 v Alnwick TownPickering Town 3-1 Alnwick Town | FA Vase First Qualifying Round |
| 7 | Tue 8 Sep | 13-2 v Horbury TownPickering Town 3-2 Horbury Town | Northern Counties East League Premier Division |
| 8 | Fri 11 Sep | 13-2 v Grangetown Boys ClubPickering Town 3-2 Grangetown Boys Club | FA Vase Second Qualifying Round |
| 9 | Tue 15 Sep | 13-0 v Tadcaster AlbionTadcaster Albion 0-3 Pickering Town | Northern Counties East League Premier Division |
| 10 | Sat 19 Sep | 12-2 v Penistone ChurchPenistone Church 2-2 Pickering Town | Northern Counties East League Premier Division |
| 11 | Sat 26 Sep | 12-1 v Retford FCPickering Town 2-1 Retford FC | Northern Counties East League Premier Division |
| 12 | Tue 29 Sep | 10-4 v Barton TownBarton Town 4-0 Pickering Town | Northern Counties East League Premier Division |
| 13 | Sat 3 Oct | 12-1 v HandsworthPickering Town 2-1 Handsworth | Northern Counties East League Premier Division |
| 14 | Tue 6 Oct | 13-1 v Dearne & DistrictPickering Town 3-1 Dearne & District | Northern Counties East League Cup Second Round |
| 15 | Tue 13 Oct | 11-1 v Dearne & DistrictPickering Town 1-1 Dearne & District | Northern Counties East League Premier Division |
| 16 | Sat 17 Oct | 11-1 v ParkgateParkgate 1-1 Pickering Town | Northern Counties East League Premier Division |
| 17 | Sat 24 Oct | 10-3 v ThackleyPickering Town 0-3 Thackley | Northern Counties East League Premier Division |
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