| Larry Winters record |
|---|
| Year | School | Won | Lost | Title |
|---|
| 2001 | Bloomington South | 17 | 6 | |
| 2002 | Bloomington South | 23 | 1 | sectional |
| 2003 | Bloomington South | 9 | 13 | |
| 2004 | Bloomington South | 11 | 11 | |
| 2005 | Bloomington South | 16 | 6 | |
| 2006 | Bloomington South | 13 | 8 | |
| 2007 | Bloomington South | 7 | 14 | |
| 2008 | Bloomington South | 16 | 5 | |
| 2009 | Bloomington South | 16 | 5 | sectional |
| 2010 | Bloomington South | 19 | 5 | sectional |
| 2011 | Bloomington South | 16 | 3 | |
| 2012 | Bloomington South | 13 | 9 | |
| 2013 | Bloomington South | 15 | 8 | |
| 2014 | Bloomington South | 17 | 6 | |
| 2015 | Bloomington South | 13 | 9 | |
| 2016 | Bloomington South | 14 | 10 | |
| 2017 | Bloomington South | 10 | 12 | |
| 2018 | Bloomington South | 12 | 11 | |
| 2019 | Bloomington South | 21 | 4 | sectional |
| 2020 | Bloomington South | 14 | 9 | |
| 2021 | Bloomington South | 11 | 8 | |
| 2022 | Bloomington South | 5 | 19 | |
| 2023 | Bloomington South | 13 | 9 | |
| 2024 | Bloomington South | 12 | 11 | |