| 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 - PLAYOFFS | |||||
| TEAMS | TIME | LOCATION | |||
| at Dr. J.M. Denison 5, Bill Crothers SS 2 | 1:00 PM | Dr J M Denison SS | |||
| Stouffville 2, at St. Augustine 1 | 2:45 PM | Dr J M Denison SS | |||
| Tuesday, October 31, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Wednesday, November 1, 2023 | |||
| TEAMS | TIME | LOCATION | |
| Thursday, November 2, 2023 - PLAYOFFS | |||
| TEAMS | TIME | LOCATION | |
| at Dr. J.M. Denison 2, Stouffville 0 | 2:00 PM | Dr J M Denison SS | |