| Season | School | Record |
|---|---|---|
| 2024-2025 | Boonville | 6-6 |
| 2023-2024 | Boonville | 5-5 |
| 2022-2023 | Boonville | 8-4 |
| 2021-2022 | Boonville | 2-7 |
| 2020-2021 | Boonville | 4-4 |
| 2019-2020 | Boonville | 5-5 |
| 2018-2019 | Boonville | 11-1 |
| 2017-2018 | Boonville | 5-5 |
| 2016-2017 | Boonville | 6-5 |
| 2015-2016 | Boonville | 7-4 |
| 2014-2015 | Charlestown | 10-3 |
| 2013-2014 | Corydon Central | 6-4 |
| 2012-2013 | Corydon Central | 8-3 |
| 2011-2012 | Corydon Central | 11-3 |
| 2010-2011 | Corydon Central | 8-2 |
| 2009-2010 | Corydon Central | 7-4 |
| 2003-2004 | Corydon Central | 8-2 |
| 2002-2003 | Corydon Central | 9-2 |
| 2001-2002 | Corydon Central | 3-7 |