| 1 | Sat 26 Jul | 101-1 v ParkgateParkgate 1-1 Pickering Town | Northern Counties East League Premier Division | 1 |
| 2 | Fri 1 Aug | 103-2 v PenrithPickering Town 3-2 Penrith | Emirates FA Cup Extra Preliminary Round | 1 |
| 3 | Tue 5 Aug | 103-2 v Golcar UnitedPickering Town 3-2 Golcar United | Northern Counties East League Premier Division | 1 |
| 4 | Tue 12 Aug | 111-1 v Campion AFCCampion AFC 1-1 Pickering Town | Northern Counties East League Premier Division | 1 |
| 5 | Wed 20 Aug | 92-0 v Easington CollieryEasington Colliery 0-2 Pickering Town | Emirates FA Cup Preliminary Round Replay | 1 |
| 6 | Wed 27 Aug | 104-1 v HandsworthHandsworth 1-4 Pickering Town | Northern Counties East League Premier Division | 1 |
| 7 | Fri 29 Aug | 105-2 v Redcar AthleticPickering Town 5-2 Redcar Athletic | Emirates FA Cup First Qualifying Round | 3 |
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