| Thursday, September 19, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Friday, September 20, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Saturday, September 21, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, September 22, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Monday, September 23, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Tuesday, September 24, 2019 | ||||||||
| TEAMS | TIME | LOCATION | ||||||
| at Dr. J.M. Denison 2, Stouffville 0 | 3:00 PM | Dr J M Denison SS | ||||||
| Stouffville 2, at Keswick High School 0 | 4:00 PM | Dr J M Denison SS | ||||||
| Sir William Mulock 2, at Keswick High School 0 | 5:00 PM | Dr J M Denison SS | ||||||
| Wednesday, September 25, 2019 | |||
| TEAMS | TIME | LOCATION | |