| Friday, October 4, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Saturday, October 5, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, October 6, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Monday, October 7, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Richmond Green SS at Tommy Douglas SS | 3:30 PM | Tommy Douglas SS | |
| Tuesday, October 8, 2019 | |||||
| TEAMS | TIME | LOCATION | |||
| Thornlea SS 2, at Maple High School 1 | 4:15 PM | Maple HS | |||
| Bill Hogarth SS 4, at St. Augustine 3 | 4:15 PM | St Augustine CHS | |||
| Wednesday, October 9, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Thursday, October 10, 2019 | ||||||||
| TEAMS | TIME | LOCATION | ||||||
| Richmond Green SS 5, at Maple High School 1 | 3:30 PM | Maple HS | ||||||
| Milliken Mills 0, at Middlefield 0 | 4:15 PM | Middlefield CI | ||||||
| at Thornlea SS 1, Tommy Douglas SS 0 | 4:15 PM | Thornlea SS | ||||||