| Tuesday, October 1, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Wednesday, October 2, 2019 | |||||||||||
| TEAMS | TIME | LOCATION | |||||||||
| at Maple High School 4, Tommy Douglas SS 1 | 3:30 PM | Maple HS | |||||||||
| Bill Hogarth SS 4, at Milliken Mills 1 | 3:00 PM | Milliken Mills HS | |||||||||
| at St. Augustine 5, Middlefield 0 | 4:15 PM | St Augustine CHS | |||||||||
| Richmond Green SS 1, at Thornlea SS 0 | 3:30 PM | Thornlea SS | |||||||||
| Thursday, October 3, 2019 | |||
| TEAMS | TIME | LOCATION | |
| 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 | |