| Monday, May 9, 2016 | |||
| TEAMS | TIME | LOCATION | |
| Markham District 26, at St. Brother Andre 8 | 3:00 PM | St Brother Andre CHS | |
| Tuesday, May 10, 2016 | |||
| TEAMS | TIME | LOCATION | |
| Wednesday, May 11, 2016 | |||||
| TEAMS | TIME | LOCATION | |||
| Bill Crothers SS 11, at Newmarket HS 6 | 4:00 PM | Newmarket HS | |||
| Richmond Green SS 17, at Richmond Hill HS 0 | 2:30 PM | Richmond Hill HS | |||
| Thursday, May 12, 2016 | |||||
| TEAMS | TIME | LOCATION | |||
| Dr. G.W. Williams 2, at Dr. J.M. Denison 1 | 2:30 PM | Dr J M Denison SS | |||
| Stephen Lewis SS 20, at Sir William Mulock 0 | 4:00 PM | Sir William Mulock | |||
| Friday, May 13, 2016 | |||
| TEAMS | TIME | LOCATION | |
| Saturday, May 14, 2016 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, May 15, 2016 | |||
| TEAMS | TIME | LOCATION | |