USTA Roadster Classic
| Year | Horse | Driver | Owner |
| 2021 | Revved N Ready | Michael Tunstall | Kieran Holahan |
| 2020 | Outer Banks | Mike Felty | Shrock Standardbreds |
| 2019 | Divide N Conquer | Jimmy Robertson | Karen Raque |
| 2018 | C U Later | Debbie Foley | Hagan Saddlebreds, Inc. |
| 2017 | Genesis | James Nichols | Covered Bridge Farm LLC |
| 2016 | Finnmaster | Steve Crabtree | Steve Crabtree |
| 2015 | Track Star | Raymond Shively | R and L LLC |
| 2014 | War Horse | Raymond Shively | Raymond Shively |
| 2013 | Taking Care of Business | Raymond Shively | Raymond Shively |
| 2012 | Blaze of Sonshine | Luman Wadhams | Ann McMurry-Cox |
| 2011 | Ice Man | Raymond Shively | Raymond Shively |
| 2010 | Belle Star | Melinda Moore | Melinda Moore |
| 2009 | S Sparrow Express | Debbie Foley | Jason Schrock |
| 2008 | Trio Bolero G | Debbie Foley | Thomas Caisse |
| 2007 | Thunderbolt | Raymond Shively | Raymond Shively |
| 2006 | Wuddacomeover | Debbie Foley | Luanne Kilday |
| 2005 | King Simcoe | Merrill Murray | Tyler Thomas and Matilda Ewald |
| 2004 | Big Red | J.D. Gardner | Douglas Covert |
| 2003 | Muddy Waters | Danette Musselman | Danette Musselman |
| 2002 | Imagine That | Ruth Gimpel | Helen Rosburg |
| 2001 | Gingerbread Man | Chappy Chapman | W.L. Chapman |
| 2000 | Kreuzyn Over | Raymond Shively | Carol Hall |
| 1999 | When And Where | Raymond Shively | DeLovely Farms |
| 1998 | Spill The Ink | Danny Bugg | Danny Bugg |
| 1997 | Power Ranger | Milward Dedmon | Edwin Freeman |