Cup Winners
| Temporada | Clube | |
| 2012/2013 |  | CF Montréal |
| 2011/2012 |  | Toronto FC |
| 2010/2011 | | Toronto FC |
| 2009/2010 | | Toronto FC |
| 2008/2009 | | Toronto FC |
| 2007/2008 | | CF Montréal |
| Temporada | Clube | |
| 2012/2013 | | CF Montréal |
| 2011/2012 | | Toronto FC |
| 2010/2011 | | Toronto FC |
| 2009/2010 | | Toronto FC |
| 2008/2009 | | Toronto FC |
| 2007/2008 | | CF Montréal |