| Saturday, May 10, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, May 11, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Monday, May 12, 2014 | |||||||||||
| TEAMS | TIME | LOCATION | |||||||||
| Dr. J.M. Denison 7, at Maple High School 6 | 4:15 PM | Maple HS | |||||||||
| at Newmarket HS 27, Dr. G.W. Williams 6 | 4:15 PM | Newmarket HS | |||||||||
| Richmond Green SS 6, at Richmond Hill HS 6 | 3:00 PM | Richmond Hill HS | |||||||||
| at Stephen Lewis SS 13, Langstaff SS 0 | 2:30 PM | Stephen Lewis SS | |||||||||
| 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 | |