| Michael S. Woolington | ||
|---|---|---|
| Year | Host/Site | Round |
| 2007 | Hebron | Sectional |
| 2008 | Kankakee Valley | Sectional |
| 2009 | Garrett | Sectional |
| 2010 | Lewis Cass | Sectional |
| 2011 | Tri-County | Sectional |
| 2012 | Rensselaer Central | Sectional |
| Triton | Regional | |
| 2013 | West Central | Sectional |
| 2014 | Culver | Sectional |
| 2015 | Woodlan | Sectional |
| 2016 | Boone Grove | Sectional |
| 2017 | University | Sectional |
| 2018 | Frankfort | Sectional |
| 2019 | Triton | Sectional |
| 2020 | Valparaiso | Sectional |