| 2022-2023 |
Greensburg |
20-7 |
| 2021-2022 |
Greensburg |
21-5 |
| 2020-2021 |
Greensburg |
17-5 |
| 2019-2020 |
Greensburg |
23-2 |
| 2018-2019 |
Greensburg |
24-2 |
| 2017-2018 |
Greensburg |
20-6 |
| 2016-2017 |
Greensburg |
17-7 |
| 2015-2016 |
Greensburg |
16-8 |
| 2014-2015 |
Greensburg |
21-4 |
| 2013-2014 |
Greensburg |
28-1 |
| 2012-2013 |
Greensburg |
26-1 |
| 2011-2012 |
Greensburg |
23-1 |
| 2010-2011 |
Greensburg |
15-8 |
| 2009-2010 |
Greensburg |
20-3 |
| 2008-2009 |
Greensburg |
16-9 |
| 2007-2008 |
Greensburg |
9-12 |
| 2006-2007 |
Greensburg |
9-13 |
| 2005-2006 |
Whiteland |
8-15 |
| 2004-2005 |
Whiteland |
8-13 |
| 2003-2004 |
Whiteland |
4-17 |
| 2002-2003 |
Southwestern (Shelbyville) |
22-5 |
| 2001-2002 |
Southwestern (Shelbyville) |
16-6 |