| Season | School | Record |
|---|---|---|
| 2023-2024 | Jay County | 8-14 |
| 2022-2023 | Jay County | 9-12 |
| 2021-2022 | Jay County | 21-5 |
| 2020-2021 | Jay County | 7-11 |
| 2018-2019 | Southwestern (Hanover) | 25-2 |
| 2017-2018 | Southwestern (Hanover) | 24-3 |
| 2016-2017 | Southwestern (Hanover) | 13-10 |
| 2015-2016 | Southwestern (Hanover) | 8-16 |
| 2014-2015 | Southwestern (Hanover) | 2-22 |
| 2013-2014 | Franklin | 16-7 |
| 2012-2013 | Franklin | 15-7 |
| 2010-2011 | Shawe Memorial | 20-4 |
| 2009-2010 | Shawe Memorial | 16-6 |
| 2008-2009 | Shawe Memorial | 13-10 |
| 2007-2008 | Shawe Memorial | 8-13 |
| 2006-2007 | Shawe Memorial | 15-9 |
| 2005-2006 | Shawe Memorial | 21-4 |
| 2004-2005 | Shawe Memorial | 15-7 |
| 2003-2004 | Shawe Memorial | 16-7 |
| 2002-2003 | Shawe Memorial | 11-13 |
| 2001-2002 | Southwestern (Hanover) | 12-9 |
| 2000-2001 | Southwestern (Hanover) | 17-5 |
| 1999-2000 | Southwestern (Hanover) | 17-4 |
| 1998-1999 | Southwestern (Hanover) | 15-7 |
| 1997-1998 | Southwestern (Hanover) | 17-10 |
| 1995-1996 | Princeton | 3-18 |
| 1994-1995 | Princeton | 14-7 |
| 1993-1994 | Princeton | 19-3 |