| Friday, September 22, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Saturday, September 23, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, September 24, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Monday, September 25, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Tuesday, September 26, 2023 | |||||
| TEAMS | TIME | LOCATION | |||
| at Milliken Mills 3, Bill Crothers SS 0 | 3:30 PM | Milliken Mills HS | |||
| at St. Augustine 4, Keswick High School 2 | 3:30 PM | St Augustine CHS | |||
| Wednesday, September 27, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Renaissance ESC 7, at Unionville HS 2 | 3:30 PM | Unionville HS | |
| Thursday, September 28, 2023 | |||||
| TEAMS | TIME | LOCATION | |||
| Keswick High School 4, at Bill Crothers SS 1 | 3:30 PM | Bill Crothers SS | |||
| Markham District 1, at Tommy Douglas SS 1 | 3:30 PM | Tommy Douglas SS | |||