| Tuesday, May 13, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Wednesday, May 14, 2014 | |||||
| TEAMS | TIME | LOCATION | |||
| Markham District 29, at Bill Crothers SS 0 | 3:00 PM | Bill Crothers SS | |||
| Richmond Green SS 8, at Dr. G.W. Williams 8 | 3:00 PM | Dr G W Williams SS | |||
| Thursday, May 15, 2014 | ||||||||
| TEAMS | TIME | LOCATION | ||||||
| at Maple High School 26, Sir William Mulock 0 | 2:30 PM | Maple HS | ||||||
| at Markham District 24, Richmond Hill HS 0 | 2:30 PM | Markham DHS | ||||||
| Dr. J.M. Denison 1, at Stephen Lewis SS 1 | 4:15 PM | Stephen Lewis SS | ||||||
| Friday, May 16, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Saturday, May 17, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, May 18, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Monday, May 19, 2014 | |||
| TEAMS | TIME | LOCATION | |