| Jonathan May record | ||||
|---|---|---|---|---|
| Year | School | Won | Lost | Title |
| 2008 | New Washington | 4 | 17 | |
| 2009 | New Washington | 14 | 11 | |
| 2010 | New Washington | 7 | 15 | |
| 2011 | New Washington | 4 | 18 | |
| 2012 | New Washington | 1 | 21 | |
| 2013 | New Washington | 9 | 13 | |
| 2014 | New Washington | 6 | 16 | |
| 2015 | New Washington | 10 | 15 | |
| 2016 | New Washington | 15 | 10 | |
| 2017 | New Washington | 20 | 10 | regional |
| 2018 | New Washington | 3 | 21 | |
| 2019 | New Washington | 9 | 15 | |
| 2020 | New Washington | 14 | 11 | |