| 1 | Tue 20 Aug 2019 | 21-2 v Ramsbottom UnitedPickering Town 1-2 Ramsbottom United |
| 2 | Mon 26 Aug 2019 | 2 0-5 v Tadcaster AlbionTadcaster Albion 5-0 Pickering Town |
| 3 | Sat 31 Aug 2019 | 61-2 v MarineMarine 2-1 Pickering Town |
| 4 | Tue 3 Sep 2019 | 60-1 v Ossett UnitedOssett United 1-0 Pickering Town |
| 5 | Tue 10 Sep 2019 | 63-2 v MossleyPickering Town 3-2 Mossley |
| 6 | Sat 14 Sep 2019 | 61-3 v Kendal TownKendal Town 3-1 Pickering Town |
| 7 | Sat 21 Sep 2019 | 61-1 v Prescot CablesPickering Town 1-1 Prescot Cables |
| 8 | Mon 23 Sep 2019 | 6 2-3 v Brighouse TownBrighouse Town 3-2 Pickering Town |
| 9 | Sat 28 Sep 2019 | 21-4 v Pontefract CollieriesPontefract Collieries 4-1 Pickering Town |
| 10 | Sat 5 Oct 2019 | 22-3 v ClitheroePickering Town 2-3 Clitheroe |
| 11 | Sat 19 Oct 2019 | 2 1-3 v DroylsdenDroylsden 3-1 Pickering Town |
| 12 | Sat 2 Nov 2019 | 60-3 v City of LiverpoolPickering Town 0-3 City of Liverpool |
| 13 | Sat 9 Nov 2019 | 60-1 v MossleyMossley 1-0 Pickering Town |
| 14 | Sat 16 Nov 2019 | 61-1 v WidnesPickering Town 1-1 Widnes |
| 15 | Sat 23 Nov 2019 | 61-8 v TraffordTrafford 8-1 Pickering Town |
| 16 | Sat 30 Nov 2019 | 64-1 v DunstonPickering Town 4-1 Dunston |
| 17 | Sat 7 Dec 2019 | 60-1 v Prescot CablesPrescot Cables 1-0 Pickering Town |
| 18 | Sat 14 Dec 2019 | 63-2 v ColnePickering Town 3-2 Colne |
| 19 | Sat 21 Dec 2019 | 6 1-4 v Workington AFCPickering Town 1-4 Workington AFC |
| 20 | Wed 1 Jan 2020 | 60-3 v Tadcaster AlbionPickering Town 0-3 Tadcaster Albion |
| 21 | Sat 4 Jan 2020 | 22-3 v Ramsbottom UnitedRamsbottom United 3-2 Pickering Town |
| 22 | Sat 11 Jan 2020 | 63-2 v Ossett UnitedPickering Town 3-2 Ossett United |
| 23 | Sat 18 Jan 2020 | 62-2 v ClitheroeClitheroe 2-2 Pickering Town |
| 24 | Sat 25 Jan 2020 | 6 2-4 v Pontefract CollieriesPickering Town 2-4 Pontefract Collieries |
| 25 | Sat 1 Feb 2020 | 60-2 v ColneColne 2-0 Pickering Town |
| 26 | Sat 8 Feb 2020 | 61-2 v Runcorn LinnetsRuncorn Linnets 2-1 Pickering Town |
| 27 | Sat 29 Feb 2020 | 6 0-1 v Brighouse TownPickering Town 0-1 Brighouse Town |
| 28 | Sat 7 Mar 2020 | 62-3 v WidnesWidnes 3-2 Pickering Town |
| 29 | Tue 10 Mar 2020 | 6 1-1 v Kendal TownPickering Town 1-1 Kendal Town |
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