| 1998 | Dino Perri | Canada
Defender of the Year Award| Year | Name | Nationality | Club | Ref. | | 2000 | Bayete Smith | Canada
| Year | Name | Nationality | Club | Ref. | | 1998 | Tom Bianchi | Canada
Harry Paul Gauss Memorial AwardFirst introduced in 2004 as the CPSL President's Award, but was renamed in 2006 in honor of Harry Gauss. The award is presented to the individual who has shown allegiance, commitment and support to the league and its member clubs.
Referee of the Year AwardThe Referee of the Year award is voted on by the CSL Referee Committee.
| Year | Name | Nationality | Ref. | | 1998 | Bill Teeuwen | Canada The Fair Play and Respect Award is awarded to the club which, in the opinion of the CSL Discipline Committee, has demonstrated good discipline on the field of play and has exhibited a high level of respect for the game officials in the regular playing season
Media and Broadcaster AwardThe Media and Broadcaster Award is awarded to the individuals who have shown interest and loyalty in reporting CSL news and matches.
| Year | Name | Role | Ref. | | 2011 | Jeremy Milani | Television producer for Rogers TV. | | | 2012 | Robin Glover | Covering and providing game reports for the CNSL, CPSL and the CSL since 1995. | | | 2012 | Enio Perruzza | For announcing CNSL, CPSL and the CSL matches for 26 years. | |
Second Division awardsMost Valuable Player AwardThe league's MVP award.
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