| 1 | Sat 26 Jul | 91-1 v ParkgateParkgate 1-1 Pickering Town | Northern Counties East League Premier Division |
| 2 | Fri 1 Aug | 93-2 v PenrithPickering Town 3-2 Penrith | Emirates FA Cup Extra Preliminary Round |
| 3 | Tue 5 Aug | 173-2 v Golcar UnitedPickering Town 3-2 Golcar United | Northern Counties East League Premier Division |
| 4 | Tue 12 Aug | 91-1 v Campion AFCCampion AFC 1-1 Pickering Town | Northern Counties East League Premier Division |
| 5 | Fri 15 Aug | 14 0-0 v Easington CollieryPickering Town 0-0 Easington Colliery | Emirates FA Cup Preliminary Round |
| 6 | Wed 20 Aug | 152-0 v Easington CollieryEasington Colliery 0-2 Pickering Town | Emirates FA Cup Preliminary Round Replay |
| 7 | Fri 22 Aug | 142-0 v Horden Community WelfarePickering Town 2-0 Horden Community Welfare | Isuzu FA Vase First Qualifying Round |
| 8 | Wed 27 Aug | 94-1 v HandsworthHandsworth 1-4 Pickering Town | Northern Counties East League Premier Division |
| 9 | Fri 29 Aug | 95-2 v Redcar AthleticPickering Town 5-2 Redcar Athletic | Emirates FA Cup First Qualifying Round |
| 10 | Wed 3 Sep | 93-2 v Eccleshill UnitedEccleshill United 2-3 Pickering Town | Northern Counties East League Premier Division |
| 11 | Fri 5 Sep | 92-1 v Wombwell TownPickering Town 2-1 Wombwell Town | Northern Counties East League Premier Division |
| 12 | Tue 9 Sep | 92-3 v Albion SportsAlbion Sports 3-2 Pickering Town | Northern Counties East League Premier Division |
| 13 | Sat 13 Sep | 90-2 v Runcorn LinnetsPickering Town 0-2 Runcorn Linnets | Emirates FA Cup Second Qualifying Round |
| 14 | Tue 16 Sep | 9 4-4 v Horbury TownPickering Town 4-4 Horbury Town | Northern Counties East League Premier Division |
| 15 | Sat 20 Sep | 90-1 v Yarm & EaglescliffePickering Town 0-1 Yarm & Eaglescliffe | Isuzu FA Vase Second Qualifying Round |
| 16 | Sat 27 Sep | 9 3-3 v Knaresborough TownPickering Town 3-3 Knaresborough Town | Northern Counties East League Premier Division |
| 17 | Tue 30 Sep | 9 2-0 v Beverley TownPickering Town 2-0 Beverley Town | Northern Counties East League Premier Division |
| 18 | Sat 4 Oct | 92-3 v ThackleyPickering Town 2-3 Thackley | Northern Counties East League Premier Division |
| 19 | Sat 11 Oct | 93-0 v Barton TownBarton Town 0-3 Pickering Town | Northern Counties East League Premier Division |
| 20 | Tue 14 Oct | 92-0 v SheffieldPickering Town 2-0 Sheffield | Northern Counties East League Premier Division |
| 21 | Sat 18 Oct | 91-5 v Bottesford TownBottesford Town 5-1 Pickering Town | Northern Counties East League Premier Division |
| 22 | Sat 1 Nov | 92-0 v Penistone ChurchPenistone Church 0-2 Pickering Town | Northern Counties East League Premier Division |
| 23 | Tue 11 Nov | 9 1-1 v Frickley AthleticFrickley Athletic 1-1 Pickering Town | Northern Counties East League Premier Division |
| 24 | Sat 15 Nov | 91-2 v ParkgatePickering Town 1-2 Parkgate | Northern Counties East League Premier Division |
| 25 | Sat 22 Nov | 90-2 v Golcar UnitedGolcar United 2-0 Pickering Town | Northern Counties East League Premier Division |
| 26 | Tue 25 Nov | 92-3 v LiversedgePickering Town 2-3 Liversedge | Northern Counties East League Cup Third Round |
| 27 | Sat 29 Nov | 90-4 v Campion AFCPickering Town 0-4 Campion AFC | Northern Counties East League Premier Division |
| 28 | Sat 13 Dec | 92-3 v SheffieldSheffield 3-2 Pickering Town | Northern Counties East League Premier Division |
| 29 | Tue 16 Dec | 90-3 v Albion SportsPickering Town 0-3 Albion Sports | Northern Counties East League Premier Division |
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