OCAA FEMALE ATHLETE OF THE YEAR
| Season | Athlete(s) | School | Sport(s) |
| 2023-24 | Breanna Pretty | Lambton | Basketball |
| 2022-23 | Bryanna Kressler | St. Clair | Softball |
| 2021-22 | Tessa Liu | Seneca | Badminton |
| 2019-20 | Chuot Angou | Fanshawe | Basketball |
| 2018-19 | Jade Kovacevic | Fanshawe | Soccer |
| 2017-18 | Ceejay Nofuente | Humber | Basketball |
| 2016-17 | Ceejay Nofuente | Humber | Basketball |
| 2015-16 | Ceejay Nofuente | Humber | Basketball |
| 2014-15 | Thalia Hanniman | Humber | Volleyball |
| 2013-14 | Kelly Nyhof | Humber | Volleyball |
| 2012-13 | Tracy Wong | Humber | Badminton |
| 2011-12 | Vicky Siemon | Humber | Cross Country |
| 2010-11 | Landis Doyle | Humber | Volleyball |
| 2009-10 | Renee Yip | Humber | Badminton |
| 2008-09 | Ashley Docking | Seneca | Soccer, Basketball |
| 2007-08 | Katie Szeghalmi | Durham | Soccer |
| 2006-07 | Megan Stacey | Nipissing | Volleyball |
| 2005-06 | Natasha Thombs | Seneca | Basketball |
| 2004-05 | Lisa Martin | Cambrian | Soccer, Volleyball |
| 2003-04 | Erin Smith | Durham | Fastball, Volleyball |
| 2002-03 | Stacey Michaels | Cambrian | Badminton |
| 2001-02 | Joanna Vitale | Humber | Soccer, Indoor Soccer |
| 2000-01 | Anita Kralt | Redeemer | Soccer, Basketball, Indoor Soccer |
| 1999-2000 | Melanie Finley & Gabe Roy | Cambrian | Badminton |
| 1998-99 | Sue Mileva | Seneca | Badminton |
| 1997-98 | Joanna Van Dyke | Durham | Fastball, Volleyball |
| 1996-97 | Marcy Skribe | Durham | Basketball |
OCAA MALE ATHLETE OF THE YEAR
| Season | Athlete(s) | School | Sport(s) |
| 2023-24 | Malachi Ramsay | Conestoga | Soccer |
| 2022-23 | Luca Uccello | Humber | Soccer |
| 2021-22 | DeQuon Cascart | Humber | Basketball |
| 2019-20 | Nick Campbell | Sheridan | Basketball |
| 2018-19 | Kyle Rooke | Mohawk | Cross Country |
| 2017-18 | Cole Jordan | Fanshawe | Volleyball |
| 2016-17 | Seth Marcaccio | Fanshawe | Cross Country |
| 2015-16 | Jesse Assing | Humber | Soccer, Badminton, Indoor Soccer |
| 2014-15 | Matt Fennell | Mohawk | Basketball |
| 2013-14 | Vadim Halimov | George Brown | Basketball |
| 2012-13 | Frankie Edgecombe | Nipissing | Volleyball |
| 2011-12 | Aminu Bello | Mohawk | Basketball |
| 2010-11 | Eric Smith | Durham | Basketball |
| 2009-10 | Ryan Talsma | Redeemer | Volleyball |
| 2008-09 | Charley Spurr | Algonquin | Basketball |
| 2007-08 | Jasmin Cull | Mohawk | Volleyball |
| 2006-07 | Loui Legakis | Algonquin | Soccer |
| 2005-06 | Peter Sniuolis | Mohawk | Volleyball |
| 2004-05 | Nathaniel Allard | Centennial | Badminton |
| 2003-04 | Glendon Thomas | Cambrian | Badminton |
| 2002-03 | Joey Martins | Loyalist | Soccer, Volleyball |
| 2001-02 | Mike Silva | Humber | Soccer, Indoor Soccer |
| 2000-01 | John Sozio | Mohawk | Soccer |
| 1999-2000 | Shane Bascoe | Sheridan | Basketball |
| 1998-99 | Bill Crowdis | Durham | Basketball |
| 1997-98 | Mike Kaytar & Bob Parnell | Cambrian | Badminton |
| 1996-97 | Todd Boys | Loyalist | Volleyball |
OCAA FEMALE ROOKIE OF THE YEAR
| Season | Athlete(s) | School | Sport(s) |
| 2023-24 | Shade Hansen | Humber | Softball |
| 2022-23 | Emily Cooper | Durham | Rugby Sevens |
OCAA MALE ROOKIE OF THE YEAR
| Season | Athlete(s) | School | Sport(s) |
| 2023-24 | Timothy Lock | Humber | Badminton |
| 2022-23 | Daniel Talmage | Humber | Golf |
OCAA COACH OF THE YEAR
| Season | Coach(es) | School | Sport(s) |
| 2023-24 | Luca Sirianni | Seneca | Women's Soccer |
| 2022-23 | Doug Wiseman | St. Clair | Women's Softball |
OCAA ATHLETIC ADMINISTRATOR OF THE YEAR
| Season | Athletic Administrator(s) | School |
| 2023-24 | Gillian McCullough | Seneca |
| 2022-23 | Ray Chateau | Humber |