| Mon | Jul 26 | B12 | North York Civic #3W | 18:30 | FC Emery 2009 | | Gil Vicente 2009 |
| Mon | Jul 26 | B12 | North York Civic Field 3E | 18:30 | Asante Academy 2009 | | NY Cosmos 2009 |
| Mon | Jul 26 | B13 | North York Civic Field 5 | 18:30 | FC Emery 2008 | 11 - 0 | North York FC 2008 |
| Tue | Jul 27 | B8/9 | North York Civic Field 4E2 | 18:30 | Asante Academy 2012 | | NY Cosmos 2012 |
| Tue | Jul 27 | B8/9 | North York Civic Field 4W1 | 18:30 | Gil Vicente 2013 | | Gladiator Academy 2012 |
| Tue | Jul 27 | B8/9 | To Be Determined | 18:30 | Asante Academy 2013 | | North York FC 2013 |
| Wed | Jul 28 | B14 | North York Civic Field 5 | 18:30 | FC Emery 2007 | 6 - 2 | Gil Vicente 2007 |
| Thu | Jul 29 | B11/11 | North York Civic #3W | 18:30 | Asante Academy 2011 | | Gil Vicente 2011 |
| Thu | Jul 29 | B11/11 | North York Civic Field 3E | 18:30 | Asante Academy 2010 | | Gil Vicente FC |
| Thu | Jul 29 | B14 | North York Civic Field 5 | 18:30 | Asante Academy 2007 | 4 - 6 | Toronto Azzurri 2007 |
| Sun | Aug 1 | B13 | North York Civic #6 | 10:00 | Canadian Futbol Club 2008 | 1 - 3 | Spartacus SA 2008 |