| 1 | Sat 26 Jul | 121-1 v ParkgateParkgate 1-1 Pickering Town | Northern Counties East League Premier Division |
| 2 | Fri 1 Aug | 23-2 v PenrithPickering Town 3-2 Penrith | Emirates FA Cup Extra Preliminary Round |
| 3 | Tue 5 Aug | 123-2 v Golcar UnitedPickering Town 3-2 Golcar United | Northern Counties East League Premier Division |
| 4 | Fri 22 Aug | 22-0 v Horden Community WelfarePickering Town 2-0 Horden Community Welfare | Isuzu FA Vase First Qualifying Round |
| 5 | Wed 27 Aug | 24-1 v HandsworthHandsworth 1-4 Pickering Town | Northern Counties East League Premier Division |
| 6 | Fri 29 Aug | 25-2 v Redcar AthleticPickering Town 5-2 Redcar Athletic | Emirates FA Cup First Qualifying Round |
| 7 | Wed 3 Sep | 23-2 v Eccleshill UnitedEccleshill United 2-3 Pickering Town | Northern Counties East League Premier Division |
| 8 | Fri 5 Sep | 2 2-1 v Wombwell TownPickering Town 2-1 Wombwell Town | Northern Counties East League Premier Division |
| 9 | Tue 9 Sep | 62-3 v Albion SportsAlbion Sports 3-2 Pickering Town | Northern Counties East League Premier Division |
| 10 | Sat 13 Sep | 140-2 v Runcorn LinnetsPickering Town 0-2 Runcorn Linnets | Emirates FA Cup Second Qualifying Round |
| 11 | Tue 16 Sep | 24-4 v Horbury TownPickering Town 4-4 Horbury Town | Northern Counties East League Premier Division |
| 12 | Sat 20 Sep | 20-1 v Yarm & EaglescliffePickering Town 0-1 Yarm & Eaglescliffe | Isuzu FA Vase Second Qualifying Round |
| 13 | Sat 27 Sep | 23-3 v Knaresborough TownPickering Town 3-3 Knaresborough Town | Northern Counties East League Premier Division |
| 14 | Tue 30 Sep | 62-0 v Beverley TownPickering Town 2-0 Beverley Town | Northern Counties East League Premier Division |
| 15 | Sat 4 Oct | 62-3 v ThackleyPickering Town 2-3 Thackley | Northern Counties East League Premier Division |
| 16 | Wed 8 Oct | 52-1 v Penistone ChurchPenistone Church 1-2 Pickering Town | Northern Counties East League Cup Second Round |
| 17 | Sat 11 Oct | 6 3-0 v Barton TownBarton Town 0-3 Pickering Town | Northern Counties East League Premier Division |
| 18 | Tue 14 Oct | 62-0 v SheffieldPickering Town 2-0 Sheffield | Northern Counties East League Premier Division |
| 19 | Sat 18 Oct | 61-5 v Bottesford TownBottesford Town 5-1 Pickering Town | Northern Counties East League Premier Division |
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