| Season | School | Record |
|---|---|---|
| 2025-2026 | North Montgomery | 1-9 |
| 2024-2025 | Barr-Reeve | 17-7 |
| 2024-2025 | North Montgomery | 5-7 |
| 2023-2024 | Barr-Reeve | 25-3 |
| 2023-2024 | North Montgomery | 6-5 |
| 2022-2023 | Barr-Reeve | 12-12 |
| 2022-2023 | North Montgomery | 5-5 |
| 2021-2022 | Barr-Reeve | 17-8 |
| 2021-2022 | North Montgomery | 4-5 |
| 2020-2021 | Barr-Reeve | 29-2 |
| 2020-2021 | North Montgomery | 5-5 |
| 2019-2020 | Barr-Reeve | 25-1 |
| 2019-2020 | North Montgomery | 6-5 |
| 2018-2019 | Barr-Reeve | 26-3 |
| 2018-2019 | North Montgomery | 4-7 |
| 2017-2018 | Vincennes Lincoln | 17-9 |
| 2017-2018 | North Montgomery | 3-7 |
| 2016-2017 | Vincennes Lincoln | 10-16 |
| 2016-2017 | North Montgomery | 5-6 |
| 2015-2016 | Wood Memorial | 20-9 |
| 2015-2016 | North Montgomery | 8-4 |
| 2014-2015 | Wood Memorial | 18-10 |
| 2014-2015 | North Montgomery | 6-4 |
| 2013-2014 | Wood Memorial | 8-16 |
| 2012-2013 | Wood Memorial | 7-16 |
| 2011-2012 | Springs Valley | 5-16 |
| 2010-2011 | Springs Valley | 10-12 |
| 2009-2010 | Springs Valley | 6-17 |
| 2008-2009 | Springs Valley | 3-18 |
| 2007-2008 | Springs Valley | 6-17 |