| Friday, October 18, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Saturday, October 19, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, October 20, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Monday, October 21, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Tuesday, October 22, 2019 | |||||||||||
| TEAMS | TIME | LOCATION | |||||||||
| Milliken Mills 2, at Bill Hogarth SS 2 | 4:15 PM | Bill Hogarth SS | |||||||||
| St. Augustine 2, at Middlefield 2 | 3:30 PM | Middlefield CI | |||||||||
| at Richmond Green SS 2, Maple High School 0 | 3:30 PM | Richmond Green SS | |||||||||
| Tommy Douglas SS 2, at Thornlea SS 2 | 3:30 PM | Tommy Douglas SS | |||||||||
| Wednesday, October 23, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Thursday, October 24, 2019 - PLAYOFFS | |||||||||||
| TEAMS | TIME | LOCATION | |||||||||
| at Bill Hogarth SS 5, Maple High School 3 | 3:30 PM | Bill Hogarth SS | |||||||||
| at Richmond Green SS 6, Middlefield 1 | 3:30 PM | Richmond Green SS | |||||||||
| at St. Augustine 1, Tommy Douglas SS 0 | 3:30 PM | St Augustine CHS | |||||||||
| Milliken Mills 3, at Thornlea SS 2 | 4:15 PM | Thornlea SS | |||||||||