The OJHL Most Gentlemanly Player Award is awarded to the player adjudged to have exhibited the best type of sportsmanship and gentlemanly conduct, combined with a high-standard and proficiency of on-ice playing ability throughout the regular season.
Year - Player - Team
- 2024-25 - David Elmy, St. Michael's Buzzers
- 2023-24 - Patrick Saini, Haliburton Huskies
- 2022-23 - Tyler Fukakusa, Toronto Jr. Canadiens
- 2021-22 - Jacob Vreugdenhil, Wellington Dukes
- 2019-20 - Griffen Fox, Trenton Golden Hawks
- 2018-19 - Grayden Gottschalk, North York Rangers
- 2017-18 - Cameron Searles, St. Michaels Buzzers
- 2016-17 - Nik Coric, Whitby Fury
- 2015-16 - Brendan Jacome, Georgetown Raiders
- 2014-15 - Steve Hladin, Georgetown Raiders
- 2013-14 - Michael Prapavessis, Toronto Lakeshore Patriots
- 2012-13 - Dean Klomp, Lindsay Muskies
- 2011-12 - Dylan Goddard, Cobourg Cougars
- 2010-11 - Zach Hyman, Hamilton Red Wings
*Awarded by Division in Previous Years
- 2009-10
- Lucas Van Natter (Aurora) OJAHL
- Jeremy Franklin (Wellington) CCHL East
- Jacob Mooney (North York) CCHL West
- 2008-09
- Jeremy McCarty (Port Hope) Ruddock
- Nathan Pageau (Hamilton) Central
- John Whitelaw (Huntsville)
- Jeremy Welsh (Oakville) MacKinnon
- 2007-08
- Richard Ryan (St. Michaels) South
- Aaron Keaney (Lindsay), Andrew Fracz (Bowmanville) East
- Tyler Swan (Couchiching) North
- Chris Dunham (Burlington) West
- 2006-07
- Phil McIhone (Pickering) South
- Dennis Zak (Cobourg) East
- Dustin Turner (Sequin) North
- Matt Ferreira (Brampton) West
- 2005-06
- Paul Kerins (North York) South
- Brad Dormiedy (Bowmanville), Chris Auger (Wellington) East
- Randy Johnson (Stouffville) North
- Kyle Zettler (Hamilton) West
- 2004-05
- Vincent Rocco (Vaughan) South
- Gavin Moore (Bancroft) East
- Same Skwarchuk (Aurora) North
- Ryan Ellis (Oakville) West
- 2003-04
- Peder Skinner (St. Michaels) South
- Rusty Masters (Port Hope) East
- Francis Walker (Aurora) North
- Sam Campbell (Hamilton) West
- 2002-03
- Oren Eizenman (Wexford) South
- Matt Caruana (Bowmanville) East
- Luke Dubbin (Couchiching) North
- Brad Efthimiou (Milton) West
- 2001-02
- Matt McIsaac (St. Michaels) South
- Darren Doherty (Cobourg) East
- Chris Gill (Newmarket) North
- Mark Mazzetti (Hamilton) West
- 2000-01
- Matthew Foy (Wexford) South
- Shannon McNevin (Peterborough) East
- Jaro Wojcicki (Couchiching) North
- Mike Bibby (Bramalea) West
- 1999-00
- Roberto Orofiamma (Vaughan) South
- Kurtis McLean (Trenton) East
- Pierre Rivard (Newmarket) North
- Mike Tarantino (Oakville) West
- 1998-99
- Ben Blakeley (Trenton) East
- Kevin Edgar (Stouffville) Central
- Mike Cammalleri (Bramalea) West
- 1997-98
- Kevin Edgar (Stouffville) East
- Matt Sirman (Streetsville), Matt McCrae (Brampton) West
- 1996-97
- David Deeves (Collingwood) East
- Eric Ellis (Hamilton) West
- 1995-96
- Tavis Morrison (Trenton) East
- Glenn Bradbury (Mississauga) West
- 1994-95
- Shawn Allard (Cobourg) East
- Ian McQueen (Streetsville) West
- 1993-94
- Ben Gorewich (Markham) East
- Mike Cox (Milton) West
- 1992-93
- Jason Cardwell (Markham) East
- Ben Davis (Caledon) West