Home History
| Canada League1 Ontario | 2024/05/04 23:00 | Masters FA v Toronto FC U20 | W | 2-4 |
| Viareggio Cup | 2017/03/18 14:00 | Dukla Praha U19 v Toronto FC U20 | L | 4-2 |
| Viareggio Cup | 2017/03/15 14:00 | Juventus U19 v Toronto FC U20 | D | 1-1 |
| Viareggio Cup | 2017/03/13 14:00 | Toronto FC U20 v Maceratese U19 | D | 3-3 |
Away History
| Canada League1 Ontario | 2024/05/18 12:00 | 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 |
| England Northern League Division One | 2021/09/11 14:00 | Yorkshire Amateur v Pickering Town | D | 0-0 |