| 2004 | 2005 | 2006 | 2007 | 2008 | 2009 | 2010 | 2011 |
| Eaton | Carlisle | Brookville (Jr. High) | Talawanda | Greenville | Brookville | Brookville | Brookville |
| Greenville | Eaton | Carlisle | Eaton | Eaton | Carlisle | Carlisle | Carlisle |
| Valley View | Valley View | Eaton | Valley View | Valley View | Eaton | Eaton | Eaton |
| Tipp City | Brookville (Junior High) | National Trail | Seton Catholic | Seton Catholic | Edgewood M.S. | Edgewood M.S. | Edgewood M.S. |
| Brookville | Middletown Madison | Talawanda | National Trail | National Trail | Greenville | Greenville | National Trail |
| Spring Valley Academy | Talawanda | Seton Catholic |
Brookville |
Carlisle |
National Trail | Talawanda (J.H.) | Talawanda |
| Middletown Madison | National Trail | Valley View | Talawanda | Talawanda | |||
| Brookville |
Valley View |