Football - Champions
| Champions | ||
|---|---|---|
| YEAR | DIVISION | SCHOOL |
| 2023-24 | Buckeye | Waynesville |
| Southwestern | Bellbrook | |
| 2022-23 | East | Bellbrook |
| West | Valley View | |
| 2021-22 | East | Bellbrook, Monroe |
| West | Eaton | |
| 2020-21 | Buckeye | Waynesville |
| Southwestern | Bellbrook | |
| 2019-20 | Buckeye | Waynesville |
| Southwestern | Franklin | |
| 2018-19 | Buckeye | Middletown Madison |
| Southwestern | Bellbrook | |
| 2017-18 | Buckeye | Middletown Madison |
| Southwestern | Valley View | |
| 2016-17 | Buckeye | Carlisle |
| Southwestern | Franklin | |
| 2015-16 | Buckeye | Middletown Madison |
| Southwestern | Brookville | |
| 2014-15 | Buckeye | Middletown Madison, Waynesville |
| Southwestern | Bellbrook | |
| 2013-14 | Buckeye | Carlisle |
| Southwestern | Franklin | |
| 2012-13 | Buckeye | Carlisle, Milton-Union |
| Southwestern | Franklin | |
| 2011-12 | Buckeye | Waynesville |
| Southwestern | Eaton, Franklin | |
| 2010-11 | Buckeye | Carlisle |
| Southwestern | Eaton | |
| 2009-10 | Buckeye | Carlisle, Monroe, Waynesville |
| Southwestern | Eaton | |
| 2008-09 | Buckeye | Waynesville |
| Southwestern | Brookville | |
| 2007-08 | Buckeye | Monroe |
| Southwestern | Milton-Union | |
| 2006-07 | Buckeye | Monroe |
| Southwestern | Eaton, Milton-Union | |
| 2005-06 | Buckeye | Waynesville |
| Southwestern | Eaton, Valley View | |
| 2004-05 | Buckeye | Carlisle |
| Southwestern | Bellbrook | |
| 2003-04 | Buckeye | Brookville |
| Southwestern | Bellbrook | |
