| Season | School | Record |
|---|---|---|
| 2014-2015 | Corydon Central | 6-4 |
| 2011-2012 | Perry Central | 5-5 |
| 2010-2011 | Perry Central | 9-4 |
| 2009-2010 | Perry Central | 9-2 |
| 2008-2009 | Perry Central | 10-1 |
| 2007-2008 | Perry Central | 11-1 |
| 2006-2007 | Perry Central | 11-2 |
| 2005-2006 | Perry Central | 13-1 |
| 2004-2005 | Perry Central | 9-2 |
| 2003-2004 | Perry Central | 7-3 |
| 2002-2003 | Perry Central | 12-2 |
| 2001-2002 | Perry Central | 14-1 |
| 2000-2001 | Perry Central | 9-5 |
| 1999-2000 | Connersville | 1-10 |
| 1998-1999 | Connersville | 0-10 |
| 1997-1998 | Connersville | 4-6 |
| 1996-1997 | Connersville | 2-7 |
| 1995-1996 | Connersville | 4-6 |
| 1994-1995 | Connersville | 3-6 |