| Tuesday, October 26, 2021 | |||
| TEAMS | TIME | LOCATION | |
| Wednesday, October 27, 2021 | |||||
| TEAMS | TIME | LOCATION | |||
| at Dr. J.M. Denison 5, Stouffville 0 | 3:30 PM | Dr J M Denison SS | |||
| at Sir William Mulock 3, Dr. G.W. Williams 0 | 4:30 PM | Dr J M Denison SS | |||
| Thursday, October 28, 2021 | |||
| TEAMS | TIME | LOCATION | |
| Friday, October 29, 2021 | |||
| TEAMS | TIME | LOCATION | |
| Saturday, October 30, 2021 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, October 31, 2021 | |||
| TEAMS | TIME | LOCATION | |
| Monday, November 1, 2021 - PLAYOFFS | ||||||||
| TEAMS | TIME | LOCATION | ||||||
| Markville 1, at Stouffville 0 | 3:45 PM | Bill Crothers SS | ||||||
| Bill Crothers SS 5, at Dr. J.M. Denison 0 | 2:00 PM | Dr J M Denison SS | ||||||
| St. Augustine 3, at Sir William Mulock 1 | 3:45 PM | Dr J M Denison SS | ||||||