Awarded to the team winning the MSL-DIV1 league final in the playoffs.

Recipients: 
2018 - Assante Wealth Management Galleons (Juan Perez) 
2017 - Windsor Court Royals (Jeff Hewitson) 
2016 - Windsor Court Royals (Jeff Hewitson) 
2015 - Rogue Galleons (Berrie Holland) 
2014 - Rogue Galleons (Berrie Holland) 
2013 - Picaroons (Wolfgang Steffe) 
2012 - Oranje (Tim Blom) 
2011 - Picaroons (Wolfgang Steffe) 
2010 - Sporting (Mario DaSilva) 
2009 - Railway Men (Andy Adshade) 
2008 - Fredericton United (Alan Roy) 
2007 - Fredericton United (Alan Roy) 
2006 - Celtic (Rick Patterson) 
2005 - Bandits (Michel Pitre)

Awarded to the team with the most points during the MSL-DIV1 regular season.

Recipients: 
2018 - Cedar Valley Investment - Fury (Otto Morales) 2017 - Picaroons (Wolfgang Steffe) 
2016 - Assante Galleons (Berrie Holland) 
2015 - Sporting (Jeff Hewitson) 
2014 - Gunners (Mark Meihuizen) 
2013 - Picaroons (Wolfgang Steffe) 
2012 - Growlers United (Alan Roy) 
2011 - Gunners (Mark Meihuizen) 
2010 - Fredericton United (Alan Roy) 
2009 - Fredericton United (Alan Roy) 
2008 - Fredericton United (Alan Roy) 
2007 - Fredericton United (Alan Roy) 
2006 - Fredericton United (Alan Roy) 
2005 - Celtic (Rick Patterson)

Awarded to the player who is the best performing player during the MSL-DIV1 regular season as voted on by the MSL-DIV1 Team Managers.

Recipients: 
2018 - Galen Smith (Royals) and Ryan McVicar (Galleons)
2017 - Kurt Schmidt (CVI Collective)
2016 - Valdis Tomsons (Assante Galleons) 
2015 - Kurt Schmidt (Sporting) 
2014 - Alain Doucet (Rogue Galleons) 
2013 - Greg Seo (Growlers United)

Awarded to the top-performing athlete in his or her first season within the MSL-DIV1 league during the regular season as voted on by the MSL-DIV1 Team Managers. 2016 is the first year this award has been presented in the MSL-DIV1.

Recipients: 
2018 - Kyle Mathers (CVI Collective)
2017 - Tammy Mallais (CVI Collective)
2016 - Mark Kennedy (Windsor Court Royals)

Awarded to the player scoring the most goals during the MSL-DIV1 regular season.

Recipients: 
2018 - Galen Smith (Windsor Court Royals) 
2017 - Abderrahim Houba (Picaroons) 
2016 - Neng Johnson (Windsor Court Royals) 
2015 - Mark Meihuizen (Gunners) 
2014 - Mark Meihuizen (Gunners) 
2013 - Mark Meihuizen (Gunners) 
2012 - Mark Meihuizen (Gunners) 
2011 - Alan Roy (Growlers United) 
2010 - Mark Meihuizen (Gunners) 
2009 - Mathurin Halaoui (Fredericton United) and Mark Meihuizen (Strikers) 
2008 - Dragan Lepir (Strikers) 
2007 - Mathurin Halaoui (Celtic) 
2006 - Alan Roy (Fredericton United) 
2005 - Felix Schwarz (Celtic)

Awarded to the Goalkeeper with the best goals against average during the MSL-DIV1 regular season. In the case of multiple keepers throughtout the season, the award would be awarded to the team.

Recipients: 
2018 - Scott Kennedy (CVI Collective) 
2017 - Jason Malone (CVI Collective) 
2016 - Scott Kennedy and John Lally (Windsor Court Royals) 
2015 - Scott Kennedy and John Lally (Sporting) 
2014 - Antoine Charbachi (Gunners) 
2013 - Nathan Langill (Growlers United)

Awarded to the leagues best defensive player during the MSL-DIV1 regular season as voted on by the MSL-DIV1 Team Managers.

Recipients: 
2018 - Jean-Francois Martel (CVI Collective)
2017 - Stipo Filopovic (CVI Collective)
2016 - Alain Doucet (Assante Galleons) 
2015 - John Ward (Gunners) 
2014 - Nick Bucknall (Fredericton Kia) 
2013 - Scott McCoy (Growlers United) 
2012 - Paul Lai Fatt (Oranje) 
2011 - Nick Bucknall (Oranje) 
2010 - Peter Colbey (Sporting FC) 
2009 - Brian Stevens (Railway Men) 
2008 - Fred Finn (Fredericton United) 
2007 - Jean-Marc Ouellette (Celtic) - (Awarded Posthumously)

Awarded annually to honour the special "character" Mark Lawrense brought to the Old Boys' club. Awarded to the player who best exemplifies the special "character" of Mark during the MSL-DIV1 regular season as voted on by the MSL-DIV1 Team Managers.

Mark was not a soccer player when he joined the Old Boys, but was an excellent athlete and a willing student. Through hard work and determination, Mark gradually became one of those indispensable players you can always count on to give his best. He played his heart out, he played by the rules, and he maintained a positive attitude regardless of the score. In selecting a recipient, the Old Boys Executive focus on three of Mark's attributes: HARDWORK... DEPENDABILITY... ATTITUDE.

Recipients: 
2018 - Luc Picard (Windsor Court Royals)
2017 - Mike O'Connor (Windsor Court Royals)
2016 - Neil Thomas (Growlers United) 
2015 - George Shirley (Gunners) 
2014 - Claude Lefebvre (Growlers United) 
2013 - Carl Richardson (Gunners) 
2012 - Jim Tree (CarStar) 
2011 - Paul Mills (Oranje) 
2010 - Dave Wagner (Celtic) 
2009 - Jingdong Tang (Sporting FC) 
2008 - Kevin Kilbride (Railway Men) 
2007 - Chris Steeves (Railway Men) 
2006 - Pat Lee (Strikers) 
2005 - Wolfgang Steffe (Arthritico Madrid) 
2004 - Mick Noftall (FSSL Red Team) 
2003 - Mark Lawrence (FFSL Red Team) - (Awarded Posthumously)

The Referee Award is awarded annually to the Official that best represents and demonstrates the following attributes: Skill, Commitment, Dedication, Improvement and Spirit while officiating MSL-DIV1 games as voted on by the MSL-DIV1 Team Managers.

1st awarded, in 2014, to Dave Macdonald as an Honorary Award in recognition for his years of service and support to the Old Boys organization through his officiating.

Recipients: 
2018 - Patrick Thompson
2017 - Phil Thompson
2016 - Phil Thompson 
2015 - Dave Macdonald 
2014 - James Sharpe 
2014 - Dave Macdonald - (Honorary Award)