Player of the year » Canada
| Year | Player |
| 2024 | Jonathan David |
| 2023 | Stephen Eustáquio |
| 2022 | Alphonso Davies |
| 2021 | Alphonso Davies |
| 2020 | Alphonso Davies |
| 2019 | Jonathan David |
| 2018 | Alphonso Davies |
| 2017 | Atiba Hutchinson |
| 2016 | Atiba Hutchinson |
| 2015 | Atiba Hutchinson |
| 2014 | Atiba Hutchinson |
| 2013 | Will Johnson |
| 2012 | Atiba Hutchinson |
| 2011 | Dwayne De Rosario |
| 2010 | Atiba Hutchinson |
| 2009 | Simeon Jackson |
| 2008 | Julian de Guzmán |
| 2007 | Dwayne De Rosario |
| 2006 | Dwayne De Rosario |
| 2005 | Dwayne De Rosario |
| 2004 | Paul Stalteri |
| 2003 | Pat Onstad |
| 2002 | Jason de Vos |
| 2001 | Paul Stalteri |
| 2000 | Craig Forrest |
| 1999 | Jim Brennan |
| 1998 | Tomasz Radzinski |
| 1997 | Mark Watson |
| 1996 | Paul Peschisolido |
| 1995 | Alex Bunbury |
| 1994 | Craig Forrest |
| 1993 | Alex Bunbury |