| 1 | Fri 1 Aug | 123-2 v PenrithPickering Town 3-2 Penrith | Emirates FA Cup Extra Preliminary Round |
| 2 | Tue 5 Aug | 143-2 v Golcar UnitedPickering Town 3-2 Golcar United | Northern Counties East League Premier Division |
| 3 | Tue 12 Aug | 81-1 v Campion AFCCampion AFC 1-1 Pickering Town | Northern Counties East League Premier Division |
| 4 | Fri 15 Aug | 8 0-0 v Easington CollieryPickering Town 0-0 Easington Colliery | Emirates FA Cup Preliminary Round |
| 5 | Wed 20 Aug | 82-0 v Easington CollieryEasington Colliery 0-2 Pickering Town | Emirates FA Cup Preliminary Round Replay |
| 6 | Wed 27 Aug | 44-1 v HandsworthHandsworth 1-4 Pickering Town | Northern Counties East League Premier Division |
| 7 | Fri 29 Aug | 85-2 v Redcar AthleticPickering Town 5-2 Redcar Athletic | Emirates FA Cup First Qualifying Round |
| 8 | Wed 3 Sep | 83-2 v Eccleshill UnitedEccleshill United 2-3 Pickering Town | Northern Counties East League Premier Division |
| 9 | Fri 5 Sep | 82-1 v Wombwell TownPickering Town 2-1 Wombwell Town | Northern Counties East League Premier Division |
| 10 | Tue 9 Sep | 122-3 v Albion SportsAlbion Sports 3-2 Pickering Town | Northern Counties East League Premier Division |
| 11 | Sat 13 Sep | 8 0-2 v Runcorn LinnetsPickering Town 0-2 Runcorn Linnets | Emirates FA Cup Second Qualifying Round |
| 12 | Tue 16 Sep | 84-4 v Horbury TownPickering Town 4-4 Horbury Town | Northern Counties East League Premier Division |
| 13 | Sat 22 Nov | 140-2 v Golcar UnitedGolcar United 2-0 Pickering Town | Northern Counties East League Premier Division |
| 14 | Tue 25 Nov | 82-3 v LiversedgePickering Town 2-3 Liversedge | Northern Counties East League Cup Third Round |
| 15 | Sat 29 Nov | 80-4 v Campion AFCPickering Town 0-4 Campion AFC | Northern Counties East League Premier Division |
| 16 | Sat 13 Dec | 82-3 v SheffieldSheffield 3-2 Pickering Town | Northern Counties East League Premier Division |
| 17 | Tue 16 Dec | 80-3 v Albion SportsPickering Town 0-3 Albion Sports | Northern Counties East League Premier Division |
| 18 | Sat 20 Dec | 124-1 v HandsworthPickering Town 4-1 Handsworth | Northern Counties East League Premier Division |
| 19 | Sat 27 Dec | 120-1 v Beverley TownBeverley Town 1-0 Pickering Town | Northern Counties East League Premier Division |
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