| Bob Bressert record | ||||
|---|---|---|---|---|
| Year | School | Won | Lost | Title |
| 2001 | South Dearborn | 14 | 7 | |
| 2002 | South Dearborn | 18 | 5 | sectional |
| 2003 | South Dearborn | 13 | 9 | |
| 2004 | South Dearborn | 13 | 8 | |
| 2005 | South Dearborn | 9 | 12 | |
| 2006 | South Dearborn | 10 | 11 | |
| 2007 | South Dearborn | 11 | 10 | |
| 2008 | South Dearborn | 13 | 8 | |
| 2009 | South Dearborn | 10 | 11 | |
| 2010 | South Dearborn | 8 | 13 | |
| 2011 | South Dearborn | 7 | 14 | |
| 2012 | South Dearborn | 11 | 10 | |
| 2013 | South Dearborn | 10 | 10 | |
| 2014 | South Dearborn | 8 | 12 | |
| 2015 | Milan | 7 | 16 | |
| 2016 | Milan | 1 | 22 | |
| 2017 | Milan | 10 | 12 | |
| 2018 | Milan | 8 | 14 | |
| 2019 | Milan | 11 | 12 | |
| 2020 | Milan | 4 | 17 | |
| 2021 | Milan | 1 | 15 | |