| Friday, October 13, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Saturday, October 14, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, October 15, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Monday, October 16, 2023 | ||||||||
| TEAMS | TIME | LOCATION | ||||||
| Stouffville 1, at Bill Crothers SS 0 | 3:00 PM | Bill Crothers SS | ||||||
| St. Augustine 4, at Markville 0 | 4:00 PM | Bill Crothers SS | ||||||
| at St. Augustine 2, Stouffville 0 | 5:00 PM | Bill Crothers SS | ||||||
| Tuesday, October 17, 2023 | |||||
| TEAMS | TIME | LOCATION | |||
| Dr. J.M. Denison 5, at Bill Hogarth SS 0 | 3:00 PM | Dr J M Denison SS | |||
| St. Brother Andre 1, at Dr. G.W. Williams 0 | 4:00 PM | Dr J M Denison SS | |||
| Wednesday, October 18, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Thursday, October 19, 2023 | ||||||||
| TEAMS | TIME | LOCATION | ||||||
| at Bill Crothers SS 3, Dr. G.W. Williams 0 | 3:00 PM | Bill Crothers SS | ||||||
| Bill Hogarth SS 1, at Dr. G.W. Williams 0 | 4:00 PM | Bill Crothers SS | ||||||
| Bill Hogarth SS 1, at Markville 0 | 5:00 PM | Bill Crothers SS | ||||||