| Tim Bless record |
|---|
| Year | School | Won | Lost | Title | Class |
|---|
| 1998 | Paoli | 7 | 4 | | 2 |
| 1999 | Paoli | 5 | 5 | | 2 |
| 2000 | Columbus North | 1 | 9 | | 5 |
| 2001 | Columbus North | 4 | 7 | | 5 |
| 2002 | Columbus North | 6 | 5 | | 5 |
| 2003 | Columbus North | 8 | 2 | | 5 |
| 2004 | Columbus North | 12 | 2 | regional | 5 |
| 2005 | Columbus North | 7 | 4 | | 5 |
| 2006 | Columbus North | 9 | 5 | regional | 5 |
| 2007 | Columbus North | 12 | 2 | regional | 5 |
| 2008 | Columbus North | 4 | 6 | | 5 |
| 2009 | Columbus North | 5 | 5 | | 5 |
| 2010 | Columbus North | 7 | 4 | | 5 |
| 2011 | Columbus North | 8 | 4 | | 5 |
| 2012 | Columbus North | 6 | 6 | | 5 |
| 2013 | Columbus North | 3 | 7 | | 6 |
| 2014 | Columbus North | 5 | 6 | | 6 |
| 2015 | Columbus North | 6 | 4 | | 6 |
| 2016 | Columbus North | 9 | 2 | | 6 |
| 2017 | Columbus North | 9 | 2 | | 6 |
| 2018 | Columbus North | 8 | 2 | | 6 |
| 2019 | Columbus North | 5 | 5 | | 6 |
| 2020 | Columbus North | 6 | 3 | | 6 |
| 2021 | Columbus North | 6 | 4 | | 6 |