| Phil Leonard record | ||||
|---|---|---|---|---|
| Year | School | Won | Lost | Title |
| 2004 | South Central (Union Mills) | 0 | 20 | |
| 2005 | Fountain Central | 2 | 19 | |
| 2006 | Fountain Central | 4 | 17 | |
| 2007 | Fountain Central | 12 | 11 | |
| 2008 | Fountain Central | 6 | 15 | |
| 2015 | South Vermillion | 10 | 14 | |
| 2016 | South Vermillion | 7 | 18 | |
| 2017 | South Vermillion | 9 | 14 | |