| Sunday, September 22, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Monday, September 23, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Tuesday, September 24, 2019 | ||||||||||||||||||||
| TEAMS | TIME | LOCATION | ||||||||||||||||||
| St. Jean De Brebeuf CHS 40, at Father Bressani 21 | 4:45 PM | Father Bressani CHS | ||||||||||||||||||
| Huron Heights 28, at Keswick High School 9 | 4:45 PM | Keswick HS | ||||||||||||||||||
| Father McGivney 35, at Markville 26 | 4:45 PM | Markville SS | ||||||||||||||||||
| Bill Hogarth SS 33, at Milliken Mills 8 | 4:45 PM | Milliken Mills HS | ||||||||||||||||||
| Markham District 35, at St. Augustine 27 | 3:30 PM | St Augustine CHS | ||||||||||||||||||
| Stephen Lewis SS 48, at Tommy Douglas SS 11 | 4:00 PM | Tommy Douglas SS | ||||||||||||||||||
| Maple High School 61, at Toronto District Christian 7 | 4:45 PM | Toronto District Christian HS | ||||||||||||||||||
| Wednesday, September 25, 2019 | |||||
| TEAMS | TIME | LOCATION | |||
| at Aurora HS 32, Richmond Hill HS 16 | 4:45 PM | Aurora HS | |||
| at Sacred Heart 43, Newmarket HS 14 | 4:45 PM | Sacred Heart CHS | |||
| Thursday, September 26, 2019 | |||||||||||||||||
| TEAMS | TIME | LOCATION | |||||||||||||||
| St. Robert 31, at Bill Hogarth SS 26 | 3:30 PM | Bill Hogarth SS | |||||||||||||||
| Sir William Mulock 39, at Keswick High School 5 | 4:45 PM | Keswick HS | |||||||||||||||
| at King City SS 47, St. Theresa Of Lisieux 40 | 4:45 PM | King City SS | |||||||||||||||
| at Maple High School 40, Father Bressani 26 | 4:45 PM | Maple HS | |||||||||||||||
| at St. Augustine 32, Markville 30 | 4:00 PM | St Augustine CHS | |||||||||||||||
| St. Jean De Brebeuf CHS 42, at Tommy Douglas SS 35 | 3:30 PM | Tommy Douglas SS | |||||||||||||||
| Friday, September 27, 2019 | |||
| TEAMS | TIME | LOCATION | |
| Saturday, September 28, 2019 | |||
| TEAMS | TIME | LOCATION | |