| 1 | 1/9/2020 | 72-3 v PenrithPenrith 3-2 Pickering Town | Emirates FA Cup Extra Preliminary Round |
| 2 | 19/9/2020 | 72-2 v Workington AFCPickering Town 2-2 Workington AFC | Northern Premier League - North West Division |
| 3 | 26/9/2020 | 71-4 v MossleyMossley 4-1 Pickering Town | Northern Premier League - North West Division |
| 4 | 29/9/2020 | 7 0-3 v Ramsbottom UnitedRamsbottom United 3-0 Pickering Town | Northern Premier League - North West Division |
| 5 | 3/10/2020 | 110-1 v DunstonPickering Town 0-1 Dunston | Northern Premier League - North West Division |
| 6 | 6/10/2020 | 152-1 v Ossett UnitedPickering Town 2-1 Ossett United | Northern Premier League - North West Division |
| 7 | 10/10/2020 | 160-1 v Kendal TownPickering Town 0-1 Kendal Town | Northern Premier League - North West Division |
| 8 | 17/10/2020 | 151-0 v TraffordPickering Town 1-0 Trafford | Buildbase FA Trophy Second Qualifying Round |
| 9 | 20/10/2020 | 141-0 v Brighouse TownPickering Town 1-0 Brighouse Town | Northern Premier League - North West Division |
| 10 | 27/10/2020 | 140-4 v MarineMarine 4-0 Pickering Town | Northern Premier League - North West Division |
| 11 | 31/10/2020 | 71-4 v Runcorn LinnetsPickering Town 1-4 Runcorn Linnets | Buildbase FA Trophy Third Qualifying Round |
| 12 | 3/11/2020 | 142-3 v Pontefract CollieriesPickering Town 2-3 Pontefract Collieries | Northern Premier League - North West Division |
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