Awarded to the team winning the CSL-DIV2 league final in the playoffs.

Recipients: 
2020 - N/A 
2019 - N/A 
2018 - N/A 
2017 - Sporting (Paul Saad) 
2016 - Rogue Galleons (Albert Webster)

Awarded to the team with the most points during the CSL-DIV2 regular season.

Recipients: 
2020 - World Auto Class United (Paul Bessery) 
2019 - RVTTC Wolves (Dave Jewett) 
2018 - RVTTC Wolves (Dave Jewett) 
2017 - Strikers (Michel Pitre) 
2016 - Gunners (Chris Steeves)

Awarded to the player who is the best performing player during the CSL-DIV2 regular season as voted on by the CSL-DIV2 Team Managers.

Recipients: 
2020 - N/A
2019 - Fred Kinney (Wolves)
2018 - Carl Duivenvoorden
2017 - Claude Lefebvre (Strikers)
2016 - Greg Seo (Sporting)

Awarded to the player scoring the most goals during the CSL-DIV2 regular season.

Recipients: 
2020 - Serban Danielescu 
2019 - Michale Ho 
2018 - Hong Yan (United) and Ahmad Sahib (Strikers) 
2017 - Gerry Van Wart (Strikers) and Sergey Sklyar (Wolves) 
2016 - Oscar Paz (Rogue Galleons)

Awarded to the Goalkeeper with the best goals against average during the CSL-DIV2 regular season. In the case of multiple keepers throughout the season, the award would be awarded to the team.

Recipients: 
2020 - World Class Auto Wolves (various) 
2019 - Antoine Charbachi (Wolves) 
2018 - Antoine Charbachi 
2017 - Antoine Charbachi (Wolves) 
2016 - Antoine Charbachi (Gunners)