The OJHL Rookie of the Year Award is awarded annually to the player adjudged to be the most proficient in his first year of competition playing in the OJHL through the regular season.
Year – Winner – Team
- 2023-24 – Matthew Manza (Toronto Patriots)
- 2022-23 – Riley Patterson (North York Rangers)
- 2021-22 – George Feragas (Toronto Jr. Canadiens)
- 2019-20 – Matteo Costantini (Buffalo Jr. Sabres)
- 2018-19 – Mitchell Weeks (Newmarket Hurricanes)
- 2017-18 – Dylan Jackson (St. Michaels Buzzers)
- 2016-17 – Mel Melconian (Aurora Tigers)
- 2015-16 – Jack Jacome (Georgetown Raiders)
- 2014-15 – Cameron Morrison (Aurora Tigers)
- 2013-14 – Jake Walman (Toronto Jr. Canadiens)
- 2012-13 – Tyler Gjurich (Buffalo Jr. Sabres)
- 2011-12 – Devon Shore (Whitby Fury)
- 2010-11 – Robert Polesello (Vaughan Vipers)
*Awarded by Division in Previous Years
- 2009-10
- Zac Hall (Couchiching) OJAHL
- Jackson Teichroeb (Bowmanville) CCHL East
- Lucas Lessio (St. Michael’s) CCHL West
- 2008-09
- Ian Watters (Ajax) Ruddock
- Joel Hanley (Newmarket) Central
- Dalton McGrath (Couchiching), Dominic Alberga (Villanova) Phillips
- Alex Guptill (Brampton) MacKinnon
- 2007-08
- Michael Catenacci (Markham) South
- Josh Shalla (Bowmanville) East
- Ethan Werek (Stouffville) North
- Andrew Bathgate (Georgetown) West
- 2006-07
- Alan Reynolds (Toronto) South
- Tavis Holden (Bowmanville) East
- Corey Trivino (Stouffville), Nicholas Vassos (Orangeville) North
- Matt Hoyle (Oakville) West
- 2005-06
- Louie Caporusso (St. Michael’s) South
- Brian Rufenach (Lindsay), Bryan Scott (Bowmanville) East
- Matt Milne (Couchiching) North
- Cody Goloubef (Milton) West
- 2004-05
- Russ Brownell (Wexford) South
- Josh Gillam (Peterborough) East
- Deron Cousens (Huntsville) North
- Tim Priamo (Burlington) West
- 2003-04
- Andrew Cogliano (St. Michael’s) South
- James Neal (Bowmanville) East
- Darren Machesney (Newmarket) North
- Aaron Barton (Georgetown) West
- 2002-03
- Oren Eizenman (Wexford) South
- Liam Reddox (Wellington) East
- Mike Sullivan (Stouffville) North
- Josh Disher (Burlington) West
- 2001-02
- Wojtek Wolski (St. Michael’s) South
- Corey Vitarelli (Peterborough) East
- Luke Dubbin (Couchiching) North
- Evan McGrath (Oakville)
- 2000-01
- Matt Christie (Pickering) South
- Robbie Schremp (Syracuse) East
- Corey Locke (Newmarket) North
- Kevin Arruda (Milton) West
- 1999-00
- Ashton McLean (Wexford) South
- Robert Gherson (Wellington) East
- Beau Moyer (Couchiching) North
- Jon Tenute (Georgetown) West
- 1998-99
- Luc Chiasson (Pickering) East
- Daniel Sisca (Markham) Central
- Kevin Kurk (Niagara) West
- 1997-98
- Jeremy Van Hoof (Lindsay), Paul Dowe (Cobourg) East
- Mike Cammalleri (Bramalea) West
- 1996-97
- Preston Mizzi (Newmarket) East
- Mark Van Arkel (Milton) West
- 1995-96
- Brett Gibson (Kingston) East
- Scott Crawford (Brampton) West
- 1994-95
- Patrick Desrochers (Barrie) East
- Adam Cologiacomo (Royal York) West
- 1993-94
- Rob Fitzgerald (Peterborough) East
- Scott Bertoli (Milton) West
- 1992-93
- Jeff Williams (Newmarket) East
- David Belitski (Royal York) West