| Monday, September 30, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Tuesday, October 1, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Wednesday, October 2, 2019 | ||||||||||||||||||||
| TEAMS | TIME | LOCATION | ||||||||||||||||||
| at Bayview SS 5, Langstaff SS 2 | 3:30 PM | Bayview SS | ||||||||||||||||||
| at Huron Heights 2, Dr. G.W. Williams 1 | 3:30 PM | Huron Heights SS | ||||||||||||||||||
| at Keswick High School 10, Our Lady Of The Lake 0 | 3:30 PM | Keswick HS | ||||||||||||||||||
| Bill Hogarth SS 1, at Milliken Mills 1 | 4:15 PM | Milliken Mills HS | ||||||||||||||||||
| at Our Lady Queen Of The World 6, Unionville HS 0 | 3:30 PM | Our Lady Queen Of The World | ||||||||||||||||||
| at Aurora HS 3, Sir William Mulock 0 | 3:30 PM | Sheppards Bush | ||||||||||||||||||
| at St. Augustine 3, Alexander Mackenzie 1 | 3:00 PM | St Augustine CHS | ||||||||||||||||||
| Thursday, October 3, 2019 | ||||||||||||||
| TEAMS | TIME | LOCATION | ||||||||||||
| Dr. G.W. Williams 2, at Dr. J.M. Denison 1 | 3:30 PM | Dr J M Denison SS | ||||||||||||
| at Maple High School 1, Woodbridge College 0 | 3:30 PM | Maple HS | ||||||||||||
| at Markville 3, Father McGivney 2 | 3:30 PM | Markville SS | ||||||||||||
| Westmount 0, at Thornlea SS 0 | 3:30 PM | Thornlea SS | ||||||||||||
| at Tommy Douglas SS 1, Stephen Lewis SS 0 | 3:30 PM | Tommy Douglas SS | ||||||||||||
| Friday, October 4, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Middlefield 1, at Markham District 0 | 2:00 PM | Markham DHS | |
| Saturday, October 5, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, October 6, 2019 | |||
| TEAMS | TIME | LOCATION | |