| 1 | Sat 26 Jul | 41-1 v ParkgateParkgate 1-1 Pickering Town | Northern Counties East League Premier Division |
| 2 | Fri 1 Aug | 43-2 v PenrithPickering Town 3-2 Penrith | Emirates FA Cup Extra Preliminary Round |
| 3 | Tue 5 Aug | 43-2 v Golcar UnitedPickering Town 3-2 Golcar United | Northern Counties East League Premier Division |
| 4 | Tue 12 Aug | 41-1 v Campion AFCCampion AFC 1-1 Pickering Town | Northern Counties East League Premier Division |
| 5 | Fri 15 Aug | 40-0 v Easington CollieryPickering Town 0-0 Easington Colliery | Emirates FA Cup Preliminary Round |
| 6 | Wed 20 Aug | 42-0 v Easington CollieryEasington Colliery 0-2 Pickering Town | Emirates FA Cup Preliminary Round Replay |
| 7 | Tue 9 Sep | 42-3 v Albion SportsAlbion Sports 3-2 Pickering Town | Northern Counties East League Premier Division |
| 8 | Sat 13 Sep | 40-2 v Runcorn LinnetsPickering Town 0-2 Runcorn Linnets | Emirates FA Cup Second Qualifying Round |
| 9 | Tue 16 Sep | 44-4 v Horbury TownPickering Town 4-4 Horbury Town | Northern Counties East League Premier Division |
| 10 | Sat 20 Sep | 40-1 v Yarm & EaglescliffePickering Town 0-1 Yarm & Eaglescliffe | Isuzu FA Vase Second Qualifying Round |
| 11 | Sat 27 Sep | 4 3-3 v Knaresborough TownPickering Town 3-3 Knaresborough Town | Northern Counties East League Premier Division |
| 12 | Tue 30 Sep | 42-0 v Beverley TownPickering Town 2-0 Beverley Town | Northern Counties East League Premier Division |
| 13 | Sat 4 Oct | 42-3 v ThackleyPickering Town 2-3 Thackley | Northern Counties East League Premier Division |
| 14 | Wed 8 Oct | 162-1 v Penistone ChurchPenistone Church 1-2 Pickering Town | Northern Counties East League Cup Second Round |
| 15 | Sat 11 Oct | 4 3-0 v Barton TownBarton Town 0-3 Pickering Town | Northern Counties East League Premier Division |
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