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| Rick Gentry |
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| Year | Host/Site | Round |
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| 1993 | Vincennes | Sectional |
| 1994 | Crawford County | Sectional |
| 1995 | Vincennes | Sectional |
| 1996 | Evansville Central | Sectional |
| 1997 | Washington | Sectional |
| 1998 | Washington | Sectional |
| 1999 | Southridge | Sectional |
| 2000 | White River Valley | Sectional |
| 2001 | South Putnam | Sectional |
| 2002 | Evansville Reitz | Sectional |
| White River Valley | Regional |
| 2003 | Clay City | Sectional |
| Seymour | Regional |
| 2004 | South Putnam | Sectional |
| Washington | Regional |
| 2005 | White River Valley | Sectional |
| Frankfort | Regional |
| 2007 | North Vermillion | Sectional |
| Franklin | Regional |
| 2008 | North Vermillion | Sectional |
| Martinsville | Regional |
| Southport | Semistate |
| 2009 | Crawford County | Sectional |
| Loogootee | Regional |
| Southport | Semistate |
| 2010 | North vermillion | Sectional |
| washington | Regional |
| 2011 | South Putnam | Sectional |
| Frankfort | Regional |
| 2012 | University | Sectional |
| Lawrence Central | Regional |
| Lafayette Jeff | Semistate |
| Indianapolis | Finals |
| 2014 | Princeton | Sectional |
| 2015 | Evansville North | Sectional |
| Washington | Regional |
| 2016 | Brown County | Sectional |
| Loogootee | Regional |
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