| 2022-2023 |
Bedford North Lawrence |
16-7 |
| 2021-2022 |
Bedford North Lawrence |
11-12 |
| 2020-2021 |
Bedford North Lawrence |
14-11 |
| 2019-2020 |
Bedford North Lawrence |
15-10 |
| 2015-2016 |
Vincennes Lincoln |
17-7 |
| 2014-2015 |
Vincennes Lincoln |
21-7 |
| 2013-2014 |
Vincennes Lincoln |
15-8 |
| 2012-2013 |
Vincennes Lincoln |
18-7 |
| 2011-2012 |
Vincennes Lincoln |
15-8 |
| 2010-2011 |
Vincennes Lincoln |
10-12 |
| 2009-2010 |
Vincennes Lincoln |
13-9 |
| 2008-2009 |
Vincennes Lincoln |
14-9 |
| 2007-2008 |
Evansville Bosse |
11-12 |
| 2006-2007 |
Evansville Bosse |
22-5 |
| 2005-2006 |
Evansville Bosse |
22-2 |
| 2004-2005 |
Boonville |
16-7 |
| 2003-2004 |
Boonville |
14-8 |
| 2002-2003 |
Boonville |
6-16 |
| 2001-2002 |
Boonville |
15-6 |
| 2000-2001 |
Boonville |
15-6 |
| 1999-2000 |
Boonville |
15-7 |
| 1998-1999 |
North Central (Farmersburg) |
10-11 |
| 1997-1998 |
North Central (Farmersburg) |
8-13 |
| 1996-1997 |
North Central (Farmersburg) |
8-14 |
| 1995-1996 |
North Central (Farmersburg) |
7-14 |
| 1993-1994 |
Washington Catholic |
3-18 |