| 1 | Sat 27 Dec | 10-1 v Beverley TownBeverley Town 1-0 Pickering Town | Northern Counties East League Premier Division |
| 2 | Sat 17 Jan | 13-1 v Rossington MainPickering Town 3-1 Rossington Main | Northern Counties East League Premier Division |
| 3 | Sat 24 Jan | 12-1 v Horbury TownHorbury Town 1-2 Pickering Town | Northern Counties East League Premier Division |
| 4 | Sat 31 Jan | 12-0 v Frickley AthleticPickering Town 2-0 Frickley Athletic | Northern Counties East League Premier Division |
| 5 | Fri 13 Feb | 12-1 v Barton TownPickering Town 2-1 Barton Town | Northern Counties East League Premier Division |
| 6 | Sat 21 Feb | 11-0 v ThackleyThackley 0-1 Pickering Town | Northern Counties East League Premier Division |
| 7 | Sat 28 Feb | 11-3 v LiversedgePickering Town 1-3 Liversedge | Northern Counties East League Premier Division |
| 8 | Sat 7 Mar | 11-2 v Rossington MainRossington Main 2-1 Pickering Town | Northern Counties East League Premier Division |
| 9 | Sat 14 Mar | 13-0 v Bottesford TownPickering Town 3-0 Bottesford Town | Northern Counties East League Premier Division |
| 10 | Tue 17 Mar | 12-0 v Eccleshill UnitedPickering Town 2-0 Eccleshill United | Northern Counties East League Premier Division |
| 11 | Sat 21 Mar | 10-3 v Tadcaster AlbionTadcaster Albion 3-0 Pickering Town | Northern Counties East League Premier Division |
| 12 | Tue 24 Mar | 14-0 v Wombwell TownWombwell Town 0-4 Pickering Town | Northern Counties East League Premier Division |
| 13 | Sat 28 Mar | 11-1 v Penistone ChurchPickering Town 1-1 Penistone Church | Northern Counties East League Premier Division |
| 14 | Tue 31 Mar | 11-1 v Knaresborough TownKnaresborough Town 1-1 Pickering Town | Northern Counties East League Premier Division |
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