| Friday, September 19, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Saturday, September 20, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, September 21, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Monday, September 22, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Tuesday, September 23, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Markham District 3, at Milliken Mills 0 | 3:00 PM | Milliken Mills HS | |
| Wednesday, September 24, 2014 | ||||||||||||||
| TEAMS | TIME | LOCATION | ||||||||||||
| Richmond Green SS 3, at Richmond Hill HS 1 | 4:15 PM | Richmond Hill HS | ||||||||||||
| at Sir William Mulock 4, Maple High School 1 | 3:00 PM | Sir William Mulock | ||||||||||||
| at Stephen Lewis SS 5, Tommy Douglas SS 0 | 4:15 PM | Stephen Lewis SS | ||||||||||||
| at Thornlea SS 2, Bayview SS 1 | 3:00 PM | Thornlea SS | ||||||||||||
| Bur Oak SS 2, at Unionville HS 1 | 4:15 PM | Unionville HS | ||||||||||||
| Thursday, September 25, 2014 | |||
| TEAMS | TIME | LOCATION | |