| 1996 | Robert Cromartie / Rhys' Pieces | |
| 1997 | Becky Hill / Rhys' Pieces | |
| 1998 | Cis Hinkle / Stringdancer | |
| 1999 | George Marshall / Wild Asparagus | |
| 2000 | Lisa Greenleaf / Nightingale | |
| 2001 | Keith Cornett, Darlene Underwood / The Groovemongers | |
| 2002 | Fri- Keith Cornett / Stringdancer, SatSun- Becky Hill / Hotpoint | |
| 2003 | Fri- Robert Cromartie, SatSun- Kathy Anderson / Flapjack | |
| 2004 | Fri- Becky Hill, SatSun- Keith Cornett / Domino | |
| 2005 | Fri- Susan Petrick, SatSun- Robert Cromartie / Airdance | |
| 2006 | Fri- Will Mentor, SatSun- Susan Kevra / The Reckless Ramblers | |
| 2007 | Fri- Darlene Underwood, SatSun- Cis Hinkle / The Groovemongers | |
| 2008 | George Marshall / Wild Asparagus | |
| 2009 | Lisa Greenleaf / Lift Ticket | |
| 2010 | Fri- Babara Ramlow, SatSun- Darlene Underwood / Crowfoot | |
| 2011 | Fri- Cary Ravitz, SatSun- Susan Petrick / The Great Bear Trio | |
| 1996 | Ron Buchanan / Fri- International Harvesters, Sat- The Berea Castoffs |
| 1997 | Ron Buchanan / Fri- International Harvesters, Sat- The Berea Castoffs |
| 1998 | Ron Buchanan / Fri- International Harvesters, Sat- The Berea Castoffs |
| 1999 | Carol Kopp / Fri- International Harvesters, Sat- The Berea Castoffs |
| 2000 | Carol Kopp / Fri- Elise Melrood, Karen Jones, David Witherspoon, and Nathan Wilson, Sat- The Berea Castoffs |
| 2001 | David Kirchner / Fri- International Harvesters, Sat- The Berea Castoffs |
| 2002 | Mark Langner / Jumpin the Gun |
| 2003 | Beth Molaro / The Berea Castoffs |
| 2004 | Fri- Steve Bennett, Sat- Susan Kevra / Changeling |
| 2005 | Carol Kopp / Hotpoint |
| 2006 | Diane Silver / Hot Club of Derbytown |
| 2007 | Ron Buchanan / Hot Club of Derbytown with Tripp Bratton |
| 2008 | Ted Hodapp / Contrarians |
| 2009 | Barbara Groh / U4 |
| 2010 | Keith Cornett Eustis / Avant Gardeners | 2011 | Gaye Fifer / Mean Lids |