| Friday, September 29, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Saturday, September 30, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, October 1, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Monday, October 2, 2023 | ||||||||
| TEAMS | TIME | LOCATION | ||||||
| Renaissance ESC 5, at Bill Crothers SS 2 | 3:00 PM | Bill Crothers SS | ||||||
| Markham District 2, at Keswick High School 0 | 3:30 PM | Keswick HS | ||||||
| St. Augustine 4, at Tommy Douglas SS 1 | 4:15 PM | Tommy Douglas SS | ||||||
| Tuesday, October 3, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Wednesday, October 4, 2023 | |||
| TEAMS | TIME | LOCATION | |
| at Markham District 4, Bill Crothers SS 1 | 3:30 PM | Markham DHS | |
| Thursday, October 5, 2023 | |||||
| TEAMS | TIME | LOCATION | |||
| at Keswick High School 1, Renaissance ESC 0 | 4:15 PM | Keswick HS | |||
| Milliken Mills 3, at Unionville HS 1 | 3:30 PM | Unionville HS | |||