| Friday, October 15, 2021 | |||
| TEAMS | TIME | LOCATION | |
| Saturday, October 16, 2021 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, October 17, 2021 | |||
| TEAMS | TIME | LOCATION | |
| Monday, October 18, 2021 | |||||
| TEAMS | TIME | LOCATION | |||
| Dr. J.M. Denison 4, at Dr. G.W. Williams 1 | 3:30 PM | Dr J M Denison SS | |||
| Sir William Mulock 3, at Stouffville 0 | 4:30 PM | Dr J M Denison SS | |||
| Tuesday, October 19, 2021 | |||
| TEAMS | TIME | LOCATION | |
| at Bill Crothers SS 7, Markville 0 | 3:30 PM | Bill Crothers SS | |
| Wednesday, October 20, 2021 | |||||
| TEAMS | TIME | LOCATION | |||
| Sir William Mulock 2, at Dr. J.M. Denison 1 | 3:30 PM | Dr J M Denison SS | |||
| at Stouffville 1, Dr. G.W. Williams 0 | 4:30 PM | Dr J M Denison SS | |||
| Thursday, October 21, 2021 | |||
| TEAMS | TIME | LOCATION | |
| at St. Augustine 5, Markville 1 | 3:30 PM | Bill Crothers SS | |