| 1 | Fri 22 Aug | 92-0 v Horden Community WelfarePickering Town 2-0 Horden Community Welfare | Isuzu FA Vase First Qualifying Round |
| 2 | Wed 27 Aug | 114-1 v HandsworthHandsworth 1-4 Pickering Town | Northern Counties East League Premier Division |
| 3 | Sat 27 Sep | 143-3 v Knaresborough TownPickering Town 3-3 Knaresborough Town | Northern Counties East League Premier Division |
| 4 | Tue 30 Sep | 72-0 v Beverley TownPickering Town 2-0 Beverley Town | Northern Counties East League Premier Division |
| 5 | Sat 4 Oct | 72-3 v ThackleyPickering Town 2-3 Thackley | Northern Counties East League Premier Division |
| 6 | Wed 8 Oct | 92-1 v Penistone ChurchPenistone Church 1-2 Pickering Town | Northern Counties East League Cup Second Round |
| 7 | Sat 1 Nov | 72-0 v Penistone ChurchPenistone Church 0-2 Pickering Town | Northern Counties East League Premier Division |
| 8 | Tue 11 Nov | 71-1 v Frickley AthleticFrickley Athletic 1-1 Pickering Town | Northern Counties East League Premier Division |
| 9 | Sat 15 Nov | 161-2 v ParkgatePickering Town 1-2 Parkgate | Northern Counties East League Premier Division |
| 10 | Sat 22 Nov | 120-2 v Golcar UnitedGolcar United 2-0 Pickering Town | Northern Counties East League Premier Division |
| 11 | Tue 25 Nov | 72-3 v LiversedgePickering Town 2-3 Liversedge | Northern Counties East League Cup Third Round |
| 12 | Sat 29 Nov | 160-4 v Campion AFCPickering Town 0-4 Campion AFC | Northern Counties East League Premier Division |
| 13 | Sat 13 Dec | 112-3 v SheffieldSheffield 3-2 Pickering Town | Northern Counties East League Premier Division |
| 14 | Tue 16 Dec | 140-3 v Albion SportsPickering Town 0-3 Albion Sports | Northern Counties East League Premier Division |
| 15 | Sat 20 Dec | 164-1 v HandsworthPickering Town 4-1 Handsworth | Northern Counties East League Premier Division |
| 16 | Sat 27 Dec | 160-1 v Beverley TownBeverley Town 1-0 Pickering Town | Northern Counties East League Premier Division |
| 17 | Sat 17 Jan | 143-1 v Rossington MainPickering Town 3-1 Rossington Main | Northern Counties East League Premier Division |
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