| Saturday, October 2, 2021 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, October 3, 2021 | |||
| TEAMS | TIME | LOCATION | |
| Monday, October 4, 2021 | |||||
| TEAMS | TIME | LOCATION | |||
| at Sir William Mulock 7, Stouffville 0 | 3:30 PM | Dr J M Denison SS | |||
| at Dr. J.M. Denison 3, Dr. G.W. Williams 0 | 4:30 PM | Dr J M Denison SS | |||
| Tuesday, October 5, 2021 | |||
| TEAMS | TIME | LOCATION | |
| at Bill Crothers SS 5, St. Augustine 0 | 3:30 PM | Bill Crothers SS | |
| Wednesday, October 6, 2021 | |||||
| TEAMS | TIME | LOCATION | |||
| Stouffville 1, at Dr. G.W. Williams 1 | 3:30 PM | Dr J M Denison SS | |||
| Dr. J.M. Denison 1, at Sir William Mulock 1 | 4:30 PM | Dr J M Denison SS | |||
| Thursday, October 7, 2021 | |||
| TEAMS | TIME | LOCATION | |
| Bill Crothers SS 5, at Markville 0 | 4:30 PM | Bill Crothers SS | |
| Friday, October 8, 2021 | |||
| TEAMS | TIME | LOCATION | |