| 2023 | WC My Casey/Rickey Harris | Ricky Harris/Cheryl Innis/Danny Hicks |
| 2022 | WC My Casey/Ricky Harris | Ricky Harris/Cheryl Innis/Danny Hicks |
| 2019 | My Casey/Ricky Harris | Ricky Harris/Cheryl Innis/Danny Hicks |
| 2018 | My Casey/Ricky Harris | Ricky Harris/Cheryl Innis/Danny Hicks |
| 2017 | Storm Trooper/Carolyn Nugent | Lloyd Nugent |
| 2016 | Storm Trooper/Carolyn Nugent | Lloyd Nugent |
| 2015 | Nordic Storm/Jim McKague | Jim McKague |
| 2014 | Emerson/Raymond Shively | Raymond Shively |
| 2013 | Storm Trooper/Carolyn Nugent | Lloyd Nugent |
| 2012 | Storm Trooper/Carolyn Nugent | Lloyd Nugent |
| 2011 | Electrical Image/Sebastien Hebert | Sebastien Hebert |
| 2010 | Cookie Monster/Mark Catron | Mark Catron |
| 2009 | Big Red/Raymond Shively | Raymond Shively |
| 2008 | Big Red/Raymond Shively | Raymond Shively |
| 2007 | Road Rage/Wayne Scharf | Shirley & Wayne Scharf |
| 2006 | Road Rage/Wayne Scharf | Shirley & Wayne Scharf |
| 2005 | Road Rage/Wayne Scharf | Shirley & Wayne Scharf |
| 2004 | Romantic Moments/Yannick LaFlamme | Yannick LaFlamme |
| 2003 | Bunker Buster/Danny Bugg | Danny Bugg |
| 2002 | Romp Away/Lawrence Carss | Mr. & Mrs. Lanny Judd |
| 2001 | The Gambler/Sam Brannon | Leatherwood Farm |
| 2000 | Midday Special/Ross McLean | Ross McLean |
| 1999 | Midday Special/Ross McLean | Ross McLean |
| 1998 | Cross Bow/Laurence Smith | Laurence Smith |
| 1997 | Ellery/Tom Oxley | Jean & Tom Oxley |
| 1996 | Midday Special/Ross McLean | Ross McLean |
| 1995 | Astrolite/Bill McWilliams | Bill McWilliams |
| 1994 | Midday Special/Ross McLean | Ross McLean |
| 1993 | Patino/Sam Brannon | Sam Brannon |
| 1992 | Bourne Decisive/Wayne Marshall | Wayne Marshall |
| 1991 | Knee Deep/Jim McKague | Jim McKague |
| 1990 | Oscar/Bill McWilliams | Bill McWilliams |
| 1989 | Friday’s Song/Bob Ross | Bob Ross |