| Canada League1 Ontario | 2024/05/04 00:00 | Pickering Town v St Catharines | W | 2-1 |
| Club Friendly List | 2023/07/25 18:45 | Bridlington Town v Pickering Town | L | 5-1 |
| England Northern League Division One | 2022/03/29 18:45 | Pickering Town v Liversedge | L | 1-3 |
| England Northern League Division One | 2022/01/18 19:45 | Marske United v Pickering Town | L | 5-2 |
| England FA Trophy | 2021/10/30 14:00 | Morpeth Town v Pickering Town | L | 4-2 |
| England FA Trophy | 2021/10/09 14:00 | Pickering Town v Ramsbottom United | W | 2-1 |
| England Northern League Division One | 2021/09/11 14:00 | Yorkshire Amateur v Pickering Town | D | 0-0 |
| UK Friendlies | 2021/07/10 14:00 | North Ferriby v Pickering Town | L | 2-0 |
| Canada League1 Ontario | 2023/07/08 00:00 | North Mississauga SC v Darby FC | D | 2-2 |