| 1 | Sat 31 Jan | 62-0 v Frickley AthleticPickering Town 2-0 Frickley Athletic | Northern Counties East League Premier Division |
| 2 | Fri 13 Feb | 62-1 v Barton TownPickering Town 2-1 Barton Town | Northern Counties East League Premier Division |
| 3 | Sat 21 Feb | 61-0 v ThackleyThackley 0-1 Pickering Town | Northern Counties East League Premier Division |
| 4 | Sat 14 Mar | 123-0 v Bottesford TownPickering Town 3-0 Bottesford Town | Northern Counties East League Premier Division |
| 5 | Tue 17 Mar | 62-0 v Eccleshill UnitedPickering Town 2-0 Eccleshill United | Northern Counties East League Premier Division |
| 6 | Sat 21 Mar | 120-3 v Tadcaster AlbionTadcaster Albion 3-0 Pickering Town | Northern Counties East League Premier Division |
| 7 | Tue 24 Mar | 24-0 v Wombwell TownWombwell Town 0-4 Pickering Town | Northern Counties East League Premier Division |
| 8 | Sat 28 Mar | 21-1 v Penistone ChurchPickering Town 1-1 Penistone Church | Northern Counties East League Premier Division |
| 9 | Tue 31 Mar | 141-1 v Knaresborough TownKnaresborough Town 1-1 Pickering Town | Northern Counties East League Premier Division |
| 10 | Sat 4 Apr | 60-2 v LiversedgeLiversedge 2-0 Pickering Town | Northern Counties East League Premier Division |
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