| Year | Pony | Driver | Owner | |||
| 2020 | Twin Willow’s McDreamy | Helen Rich Odessa, FL | ||||
| 2019 | Prime Time’s Choice LF | Golden Creek Farms, Inc. Simpsonville, KY | ||||
| 2018 | Twin Willow’s McDreamy | Helen Rich Odessa, FL | ||||
| 2017 | Twin Willow’s McDreamy | Helen Rich Odessa, FL | ||||
| 2016 | Twin Willow’s McDreamy | Helen Rich Odessa, FL | ||||
| 2015 | Twin Willow’s McDreamy | Helen Rich Odessa, FL | ||||
| 2014 | Twin Willow’s McDreamy | Deborah Jahn Chicago, IL | ||||
| 2013 | Twin Willow’s McDreamy | Deborah Jahn Chicago, IL | ||||
| 2012 | CHCalvin Hobbs (CAN) | James R. Dellinger, Jr. Cartersville, GA | ||||
| 2011 | Regal’s Lightning Strike LF | Josh Greer East Bernstadt, KY | ||||
| 2010 | Beaulah Jean | Mary Gaylord McClean Simpsonville, KY | ||||
| 2009 | Beaulah Jean | Mary Gaylord McClean Simpsonville, KY | ||||
| 2008 | Beaulah Jean | Mary Gaylord McClean Simpsonville, KY | ||||
| 2007 | CHFree Willy | Georgia H. Blevins Bowling Green, KY | ||||
| 2006 | CHFree Willy | Georgia H. Blevins Bowling Green, KY | ||||
| 2005 | CHCalvin Hobbs (CAN) | Priscilla C. Gise Revocable Trust Minnetonka, MN | ||||
| 2004 | Desert Prince | Helen Rosburg Odessa, FL | ||||
| 2003 | Desert Prince | Helen Rosburg Odessa, FL | ||||
| 2002 | Heartland Production | Mary Gaylord McClean Simpsonville, KY | ||||
| 2001 | Lamborghini | Laurel Nelson Versailles, KY | ||||
| 2000 | CHFree Willy | Susan Phillips Atlanta, GA | ||||
| 1999 | Desert Prince | Douglass Mesker Tampa, FL | ||||
| 1998 | Desert Prince | Douglass Mesker Tampa, FL | ||||
| 1997 | I’ve Arrived | Ed Moore Dunwoody, GA |
