| Monday, October 21, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Tuesday, October 22, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Wednesday, October 23, 2019 | |||||||||||
| TEAMS | TIME | LOCATION | |||||||||
| Bill Crothers SS 4, at St. Brother Andre 0 | 2:00 PM | Milliken Mills HS | |||||||||
| Bill Crothers SS 5, at Thornhill SS 0 | 3:00 PM | Milliken Mills HS | |||||||||
| at St. Augustine 1, St. Brother Andre 0 | 4:00 PM | Milliken Mills HS | |||||||||
| St. Augustine 2, at Thornhill SS 0 | 5:00 PM | Milliken Mills HS | |||||||||
| Thursday, October 24, 2019 - PLAYOFFS | |||||
| TEAMS | TIME | LOCATION | |||
| Bill Crothers SS 6, at Newmarket HS 0 | 1:30 PM | Dr J M Denison SS | |||
| at Dr. J.M. Denison 1, St. Augustine 0 | 3:00 PM | Dr J M Denison SS | |||
| Friday, October 25, 2019 - PLAYOFFS | |||
| TEAMS | TIME | LOCATION | |
| at Bill Crothers SS 5, Dr. J.M. Denison 0 | 2:30 PM | Dr J M Denison SS | |
| Saturday, October 26, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, October 27, 2019 | |||
| TEAMS | TIME | LOCATION | |