| Monday, May 19, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Tuesday, May 20, 2014 | |||||||||||
| TEAMS | TIME | LOCATION | |||||||||
| at Dr. J.M. Denison 14, Langstaff SS 0 | 3:00 PM | Dr J M Denison SS | |||||||||
| Newmarket HS 31, at Richmond Green SS 6 | 4:15 PM | Richmond Green SS | |||||||||
| at Richmond Hill HS 7, Bill Crothers SS 0 | 2:30 PM | Richmond Hill HS | |||||||||
| Maple High School 15, at Stephen Lewis SS 12 | 3:00 PM | Stephen Lewis SS | |||||||||
| Wednesday, May 21, 2014 | |||||
| TEAMS | TIME | LOCATION | |||
| Sir William Mulock 0, at Langstaff SS 0 | 4:15 PM | Langstaff SS | |||
| at Markham District 28, Dr. G.W. Williams 0 | 3:00 PM | Markham DHS | |||
| Thursday, May 22, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Friday, May 23, 2014 | |||
| TEAMS | TIME | LOCATION | |
| at Newmarket HS 21, Richmond Hill HS 0 | 4:00 PM | Newmarket HS | |
| Saturday, May 24, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, May 25, 2014 | |||
| TEAMS | TIME | LOCATION | |