The OJHL Executive of the Year Award is awarded annually to the Executive, that is adjudged to have exceeded expectations in his role with the club throughout the course of the regular season. In 2022-23 the award was changed to only include team executives including Governors, Presidents, Vice Presidents and high level business operations personnel. Prior to this time, the award included President, Vice-President, General Manager, Assistant General Manager and Marketing Executives. The award was presented for the first time following the 2011-12 season
Year – Execitive – Team
- 2023-24 – Dave Steele, Collingwood Blues
- 2022-23 – Jason Tryfon, Milton Menace
- 2021-22 – Blake Ricci, Toronto Jr. Canadiens
- 2019-20 – Peter Goulet, Trenton Golden Hawks
- 2018-19 – Claude Desjardins, North York Rangers
- 2017-18 – Mark Joslin, Toronto Patriots
- 2016-17 – Greg Walters, Georgetown Raiders
- 2015-16 – John McDonald, Trenton Golden Hawks
- 2014-15 – Rob Campbell, Oakville Blades
- 2013-14 – Mike Tarantino, Toronto Lakeshore Patriots
- 2012-13 – Michael Peca, Buffalo Jr. Sabres
- 2011-12 – Ken Burrows, Stouffville Spirit