| Friday, October 27, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Saturday, October 28, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, October 29, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Monday, October 30, 2023 | |||||||||||
| TEAMS | TIME | LOCATION | |||||||||
| at Bill Crothers SS 36, Bur Oak SS 32 | 3:45 PM | Bill Crothers SS | |||||||||
| St. Maximilian 64, at Cardinal Carter 9 | 3:45 PM | Cardinal Carter CHS | |||||||||
| at Newmarket HS 31, Huron Heights 24 | 3:45 PM | Newmarket HS | |||||||||
| Sir William Mulock 23, at Sacred Heart 13 | 4:00 PM | Sacred Heart CHS | |||||||||
| Tuesday, October 31, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Wednesday, November 1, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Thursday, November 2, 2023 - PLAYOFFS | |||||||||||||||||
| TEAMS | TIME | LOCATION | |||||||||||||||
| Markham District 15, at Bill Crothers SS 0 | 3:45 PM | Bill Crothers SS | |||||||||||||||
| Bayview SS 31, at Maple High School 28 | 3:45 PM | Maple HS | |||||||||||||||
| at St. Elizabeth 39, St. Joan Of Arc 20 | 3:45 PM | St Elizabeth CHS | |||||||||||||||
| Alexander Mackenzie 31, at St. Jean De Brebeuf CHS 16 | 3:00 PM | St Jean De Brebeuf CHS | |||||||||||||||
| at Stouffville 49, St. Brother Andre 47 | 3:45 PM | Stouffville DSS | |||||||||||||||
| Holy Cross 29, at Tommy Douglas SS 15 | 3:15 PM | Tommy Douglas SS | |||||||||||||||