Home History
| Canada League1 Ontario | 2024/05/04 23:00 | Masters FA v Toronto FC U20 | L | 2-4 |
| Canada League1 Ontario | 2024/04/28 00:00 | Unionville Milliken SC v Masters FA | L | 1-0 |
| Canada League1 Ontario | 2023/08/05 19:00 | Unionville Milliken SC v Masters FA | W | 2-3 |
| Canada League1 Ontario | 2023/07/31 00:30 | Vaughan Azzurri v Masters FA | L | 4-0 |
| Canada Championships | 2021/08/21 19:00 | York United FC v Masters FA | L | 5-0 |
Away History
| Canada League1 Ontario | 2024/05/25 19:00 | Toronto FC U20 v Pickering Town | L | 6-0 |
| Canada League1 Ontario | 2024/05/17 23:53 | Pickering Town v Darby FC | D | 1-1 |
| 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 |