| Season | School | Record |
|---|---|---|
| 2021-2022 | Tell City | 2-22 |
| 2019-2020 | Salem | 11-12 |
| 2018-2019 | Salem | 14-11 |
| 2017-2018 | Shawe Memorial | 5-20 |
| 2016-2017 | South Dearborn | 5-19 |
| 2015-2016 | South Dearborn | 1-23 |
| 2014-2015 | Crawford County | 17-7 |
| 2013-2014 | Crawford County | 18-4 |
| 2012-2013 | Crawford County | 14-8 |
| 2011-2012 | Crawford County | 19-4 |
| 2010-2011 | Crawford County | 17-6 |
| 2009-2010 | Crawford County | 15-7 |
| 2008-2009 | Crawford County | 13-9 |
| 2007-2008 | Crawford County | 5-16 |
| 2006-2007 | Paoli | 11-13 |
| 2005-2006 | Paoli | 12-10 |
| 2004-2005 | Paoli | 15-7 |
| 2003-2004 | Paoli | 11-9 |
| 2001-2002 | Paoli | 20-6 |
| 2000-2001 | Paoli | 15-10 |
| 1999-2000 | Paoli | 20-8 |
| 1998-1999 | Paoli | 22-5 |
| 1997-1998 | Paoli | 19-6 |
| 1996-1997 | Paoli | 14-8 |
| 1995-1996 | Paoli | 4-17 |
| 1994-1995 | Paoli | 4-19 |
| 1993-1994 | Paoli | 24-4 |