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| Kevin Woolsey |
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| Year | Host/Site | Round |
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| 2006 | Loogootee | Sectional |
| 2007 | Southridge | Sectional |
| 2008 | Forest Park | Sectional |
| 2010 | Forest Park | Sectional |
| 2011 | White River Valley | Sectional |
| Southridge | Regional |
| 2012 | Southridge | Sectional |
| 2013 | Boonville | Sectional |
| 2014 | White River Valley | Sectional |
| 2015 | Boonville | Sectional |
| Southridge | Regional |
| 2016 | Jasper | Sectional |
| Washington | Regional |
| 2017 | Evansville North | Sectional |
| 2018 | Loogootee | Sectional |
| Southridge | Regional |
| 2019 | Forest Park | Sectional |
| 2020 | Boonville | Sectional |
| 2021 | Southridge | Sectional |
| 2022 | Tell City | Sectional |
| Loogootee | Regional |
| 2023 | North Knox | Sectional |
| 2024 | Boonville | Sectional |
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