| 1 | Sat 26 Jul | 71-1 v ParkgateParkgate 1-1 Pickering Town |
| 2 | Tue 5 Aug | 73-2 v Golcar UnitedPickering Town 3-2 Golcar United |
| 3 | Tue 12 Aug | 71-1 v Campion AFCCampion AFC 1-1 Pickering Town |
| 4 | Wed 27 Aug | 74-1 v HandsworthHandsworth 1-4 Pickering Town |
| 5 | Wed 3 Sep | 73-2 v Eccleshill UnitedEccleshill United 2-3 Pickering Town |
| 6 | Tue 16 Sep | 74-4 v Horbury TownPickering Town 4-4 Horbury Town |
| 7 | Sat 27 Sep | 73-3 v Knaresborough TownPickering Town 3-3 Knaresborough Town |
| 8 | Tue 30 Sep | 22-0 v Beverley TownPickering Town 2-0 Beverley Town |
| 9 | Sat 4 Oct | 22-3 v ThackleyPickering Town 2-3 Thackley |
| 10 | Sat 11 Oct | 23-0 v Barton TownBarton Town 0-3 Pickering Town |
| 11 | Tue 14 Oct | 22-0 v SheffieldPickering Town 2-0 Sheffield |
| 12 | Sat 18 Oct | 21-5 v Bottesford TownBottesford Town 5-1 Pickering Town |
| 13 | Sat 1 Nov | 2 2-0 v Penistone ChurchPenistone Church 0-2 Pickering Town |
| 14 | Tue 11 Nov | 21-1 v Frickley AthleticFrickley Athletic 1-1 Pickering Town |
| 15 | Sat 15 Nov | 21-2 v ParkgatePickering Town 1-2 Parkgate |
| 16 | Sat 22 Nov | 2 0-2 v Golcar UnitedGolcar United 2-0 Pickering Town |
| 17 | Sat 29 Nov | 20-4 v Campion AFCPickering Town 0-4 Campion AFC |
| 18 | Tue 16 Dec | 20-3 v Albion SportsPickering Town 0-3 Albion Sports |
| 19 | Sat 20 Dec | 74-1 v HandsworthPickering Town 4-1 Handsworth |
| 20 | Sat 27 Dec | 70-1 v Beverley TownBeverley Town 1-0 Pickering Town |
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