| Canadian Soccer League | 2023/07/08 22:00 | Scarborough v Ooty Black Pearl FC | L | 5-0 |
| Canadian Soccer League | 2023/06/24 22:00 | Ooty Black Pearl FC v Toronto Falcons | L | 0-1 |
| Canadian Soccer League | 2023/06/17 18:00 | Weston United FC v Ooty Black Pearl FC | D | 1-1 |
| Canadian Soccer League | 2023/06/10 20:00 | Ooty Black Pearl FC v Hamilton City | L | 1-2 |
| Canadian Soccer League | 2023/05/28 20:00 | Serbian WE v Ooty Black Pearl FC | L | 4-2 |
| Canadian Soccer League | 2023/07/08 20:00 | Hamilton City v Dynamo Toronto FC | W | 0-3 |
| Canadian Soccer League | 2023/06/17 20:00 | Toronto Falcons v Dynamo Toronto FC | W | 1-2 |
| Canadian Soccer League | 2023/06/03 22:00 | Dynamo Toronto FC v Serbian WE | L | 0-3 |
| Canadian Soccer League | 2023/05/28 22:00 | Dynamo Toronto FC v Weston United FC | W | 4-1 |