| 1 | Sat 1 Dec 2018 | 9 0-0 v StamfordStamford 0-0 Pickering Town |
| 2 | Sat 22 Dec 2018 | 9 1-5 v SheffieldPickering Town 1-5 Sheffield |
| 3 | Wed 26 Dec 2018 | 91-0 v Tadcaster AlbionTadcaster Albion 0-1 Pickering Town |
| 4 | Tue 1 Jan 2019 | 91-0 v Marske UnitedPickering Town 1-0 Marske United |
| 5 | Sat 5 Jan 2019 | 90-2 v Carlton TownPickering Town 0-2 Carlton Town |
| 6 | Sat 19 Jan 2019 | 120-2 v Stocksbridge Park SteelsPickering Town 0-2 Stocksbridge Park Steels |
| 7 | Sat 26 Jan 2019 | 9 1-3 v SheffieldSheffield 3-1 Pickering Town |
| 8 | Sat 9 Feb 2019 | 91-1 v Morpeth TownPickering Town 1-1 Morpeth Town |
| 9 | Tue 12 Feb 2019 | 9 1-3 v AFC MansfieldPickering Town 1-3 AFC Mansfield |
| 10 | Sat 16 Feb 2019 | 90-1 v Ossett UnitedPickering Town 0-1 Ossett United |
| 11 | Sat 23 Feb 2019 | 91-2 v Cleethorpes TownCleethorpes Town 2-1 Pickering Town |
| 12 | Sat 2 Mar 2019 | 90-2 v Cleethorpes TownPickering Town 0-2 Cleethorpes Town |
| 13 | Sat 9 Mar 2019 | 92-1 v GresleyGresley 1-2 Pickering Town |
| 14 | Sat 23 Mar 2019 | 93-3 v StamfordPickering Town 3-3 Stamford |
| 15 | Sat 6 Apr 2019 | 91-1 v Spalding UnitedPickering Town 1-1 Spalding United |
| 16 | Tue 9 Apr 2019 | 92-3 v Pontefract CollieriesPontefract Collieries 3-2 Pickering Town |
| 17 | Sat 13 Apr 2019 | 9 0-2 v Brighouse TownPickering Town 0-2 Brighouse Town |
| 18 | Tue 16 Apr 2019 | 9 1-4 v Morpeth TownMorpeth Town 4-1 Pickering Town |
| 19 | Sat 20 Apr 2019 | 91-1 v Wisbech TownWisbech Town 1-1 Pickering Town |
| 20 | Mon 22 Apr 2019 | 91-1 v Tadcaster AlbionPickering Town 1-1 Tadcaster Albion |
| 21 | Sat 27 Apr 2019 | 15 1-5 v Loughborough DynamoPickering Town 1-5 Loughborough Dynamo |
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