| Trent Olson record | |||||
|---|---|---|---|---|---|
| Year | School | Won | Lost | Title | Class |
| 2001 | North Central (Farmersburg) | 8 | 3 | 1 | |
| 2002 | North Central (Farmersburg) | 0 | 10 | 1 | |
| 2003 | North Central (Farmersburg) | 3 | 6 | 1 | |
| 2004 | North Central (Farmersburg) | 6 | 5 | 1 | |
| 2007 | Sullivan | 7 | 3 | 2 | |
| 2008 | Sullivan | 2 | 8 | 2 | |
| 2009 | Sullivan | 4 | 6 | 2 | |
| 2010 | Sullivan | 3 | 7 | 2 | |
| 2011 | Sullivan | 6 | 4 | 2 | |
| 2012 | Sullivan | 6 | 4 | 2 | |
| 2013 | Sullivan | 7 | 4 | 2 | |
| 2014 | Sullivan | 5 | 5 | 2 | |
| 2015 | Sullivan | 8 | 3 | 3 | |
| 2016 | Sullivan | 10 | 2 | 3 | |