| Saturday, May 24, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, May 25, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Monday, May 26, 2014 | |||||||||||
| TEAMS | TIME | LOCATION | |||||||||
| Richmond Green SS 6, at Bill Crothers SS 6 | 4:15 PM | Bill Crothers SS | |||||||||
| at Dr. G.W. Williams 8, Richmond Hill HS 6 | 3:00 PM | Dr G W Williams SS | |||||||||
| Maple High School 12, at Langstaff SS 0 | 2:30 PM | Langstaff SS | |||||||||
| Stephen Lewis SS 6, at Sir William Mulock 0 | 4:15 PM | Sir William Mulock | |||||||||
| Tuesday, May 27, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Dr. J.M. Denison 19, at Sir William Mulock 0 | 3:00 PM | Sir William Mulock | |
| Wednesday, May 28, 2014 | |||||
| TEAMS | TIME | LOCATION | |||
| Dr. G.W. Williams 6, at Bill Crothers SS 0 | 4:15 PM | Bill Crothers SS | |||
| at Markham District 28, Newmarket HS 0 | 2:30 PM | Markham DHS | |||
| Thursday, May 29, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Friday, May 30, 2014 | |||
| TEAMS | TIME | LOCATION | |