| Sunday, September 29, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Monday, September 30, 2019 | |||
| TEAMS | TIME | LOCATION | |
| St. Robert 34, at Father McGivney 29 | 3:30 PM | Father Michael McGivney CA | |
| Tuesday, October 1, 2019 | |||
| TEAMS | TIME | LOCATION | |
| at Father Bressani 38, Toronto District Christian 9 | 3:30 PM | Father Bressani CHS | |
| Wednesday, October 2, 2019 | ||||||||||||||||||||
| TEAMS | TIME | LOCATION | ||||||||||||||||||
| at Dr. G.W. Williams 50, Aurora HS 38 | 4:45 PM | Dr G W Williams SS | ||||||||||||||||||
| Newmarket HS 50, at Keswick High School 10 | 4:45 PM | Keswick HS | ||||||||||||||||||
| Father McGivney 53, at Milliken Mills 13 | 4:00 PM | Milliken Mills HS | ||||||||||||||||||
| at St. Augustine 29, Bill Hogarth SS 21 | 4:00 PM | St Augustine CHS | ||||||||||||||||||
| at St. Theresa Of Lisieux 36, Cardinal Carter 26 | 3:30 PM | St Theresa Of Lisieux CHS | ||||||||||||||||||
| at Stephen Lewis SS 44, St. Jean De Brebeuf CHS 30 | 4:00 PM | Stephen Lewis SS | ||||||||||||||||||
| Sir William Mulock 57, at Sutton District 16 | 4:45 PM | Sutton DHS | ||||||||||||||||||
| Thursday, October 3, 2019 | |||||||||||
| TEAMS | TIME | LOCATION | |||||||||
| Sacred Heart 39, at Huron Heights 26 | 4:45 PM | Huron Heights SS | |||||||||
| Tommy Douglas SS 39, at Maple High School 35 | 4:00 PM | Maple HS | |||||||||
| at Markville 40, Markham District 23 | 3:30 PM | Markville SS | |||||||||
| at St. Theresa Of Lisieux 44, Richmond Hill HS 29 | 3:30 PM | St Theresa Of Lisieux CHS | |||||||||
| Friday, October 4, 2019 | |||
| TEAMS | TIME | LOCATION | |
| at Dr. J.M. Denison 40, Newmarket HS 38 | 3:30 PM | Dr J M Denison SS | |
| Saturday, October 5, 2019 | |||
| TEAMS | TIME | LOCATION | |