| Friday, September 26, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Saturday, September 27, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Sunday, September 28, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Monday, September 29, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Tuesday, September 30, 2014 | |||
| TEAMS | TIME | LOCATION | |
| at Markham District 5, Unionville HS 0 | 4:15 PM | Markham DHS | |
| Wednesday, October 1, 2014 | |||||||||||
| TEAMS | TIME | LOCATION | |||||||||
| Thornlea SS 5, at Alexander Mackenzie 1 | 4:15 PM | Alexander Mackenzie HS | |||||||||
| Stephen Lewis SS 3, at Langstaff SS 2 | 4:15 PM | Langstaff SS | |||||||||
| at Richmond Green SS 2, Bayview SS 0 | 4:15 PM | Richmond Green SS | |||||||||
| at St. Brother Andre 5, Milliken Mills 1 | 3:00 PM | St Brother Andre CHS | |||||||||
| Thursday, October 2, 2014 | |||
| TEAMS | TIME | LOCATION | |
| Sir William Mulock 2, at Tommy Douglas SS 1 | 4:15 PM | Tommy Douglas SS | |