| Year | Winner | School/District |
|---|---|---|
| 1988 | Fr. Harry Jansing | Trinity High |
| 1989 | Bob Jacobs | duPont Manual High |
| 1990 | Jim Watkins | Southern High |
| 1991 | Stan Steidel | Dayton High |
| 1992 | Paul Dennison | Western High |
| 1993 | Karen Vanover | Lafayette High |
| 1994 | Jerry Mayes | St. Xavier High |
| 1995 | Kathy Johnston | Bourbon County High |
| 1996 | Jim Komara | Fayette County High |
| 1997 | Russ Kline | Pleasure Ridge Park High |
| 1998 | Tasso Harris | Valley High |
| 1999 | Faye Thornton | Harrison County High |
| 2000 | Bob Ball | Moore Traditional High |
| 2001 | Gary Kidwell | Lewis County High |
| 2002 | Jeff Perkins | Somerset High |
| 2003 | Gene Heffington | Oldham County High |
| 2004 | Jeff Edwards | Jeffersontown High |
| 2005 | Gale Travis | Madisonville North Hopkins High |
| 2006 | Phil Rison | Montgomery County High |
| 2007 | Hugh McReynolds | Logan County High |
| 2008 | Mitchell Irvin | South Oldham High |
| 2009 | Charles Temple | Jessamine County Schools |
| 2010 | Scott Greenwald | Seneca High |
| 2011 | Arthur Ballard | Estill County High |
| 2012 | Joe Ruddell | Tates Creek High |
| 2013 | Jerry Wyman | Jefferson County Schools |
| 2014 | Victor Black | Casey County High |
| 2015 | Sam Sparks | Russell Schools |
| 2016 | Charles Patton | Ohio County High |
