| 1 | Fri 1 Aug | 173-2 v PenrithPickering Town 3-2 Penrith | Emirates FA Cup Extra Preliminary Round |
| 2 | Tue 5 Aug | 163-2 v Golcar UnitedPickering Town 3-2 Golcar United | Northern Counties East League Premier Division |
| 3 | Fri 22 Aug | 172-0 v Horden Community WelfarePickering Town 2-0 Horden Community Welfare | Isuzu FA Vase First Qualifying Round |
| 4 | Wed 27 Aug | 174-1 v HandsworthHandsworth 1-4 Pickering Town | Northern Counties East League Premier Division |
| 5 | Fri 29 Aug | 175-2 v Redcar AthleticPickering Town 5-2 Redcar Athletic | Emirates FA Cup First Qualifying Round |
| 6 | Wed 3 Sep | 63-2 v Eccleshill UnitedEccleshill United 2-3 Pickering Town | Northern Counties East League Premier Division |
| 7 | Fri 5 Sep | 62-1 v Wombwell TownPickering Town 2-1 Wombwell Town | Northern Counties East League Premier Division |
| 8 | Sat 13 Sep | 160-2 v Runcorn LinnetsPickering Town 0-2 Runcorn Linnets | Emirates FA Cup Second Qualifying Round |
| 9 | Tue 16 Sep | 64-4 v Horbury TownPickering Town 4-4 Horbury Town | Northern Counties East League Premier Division |
| 10 | Sat 20 Sep | 60-1 v Yarm & EaglescliffePickering Town 0-1 Yarm & Eaglescliffe | Isuzu FA Vase Second Qualifying Round |
| 11 | Wed 8 Oct | 42-1 v Penistone ChurchPenistone Church 1-2 Pickering Town | Northern Counties East League Cup Second Round |
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