| 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 | |||
| at Pierre Elliott Trudeau 107, Richmond Hill HS 24 | 12:45 PM | Fairtree Cricket Grounds | |||
| at Maple High School 60, Stephen Lewis SS 57 | 9:15 AM | Fairtree Cricket Grounds | |||
| Tuesday, September 30, 2014 | |||||
| TEAMS | TIME | LOCATION | |||
| Father McGivney 41, at Bill Crothers SS 40 | 12:45 PM | Fairtree Cricket Grounds | |||
| at Bur Oak SS 69, Middlefield 38 | 9:15 AM | Fairtree Cricket Grounds | |||
| Wednesday, October 1, 2014 | |||||
| TEAMS | TIME | LOCATION | |||
| Richmond Hill HS 78, at Maple High School 72 | 12:45 PM | Fairtree Cricket Grounds | |||
| Pierre Elliott Trudeau 127, at Stephen Lewis SS 40 | 9:15 AM | Fairtree Cricket Grounds | |||
| Thursday, October 2, 2014 | |||||
| TEAMS | TIME | LOCATION | |||
| Middlefield 93, at Bill Crothers SS 42 | 12:45 PM | Fairtree Cricket Grounds | |||
| at Bur Oak SS 127, Father McGivney 80 | 9:15 AM | Fairtree Cricket Grounds | |||