| 2019 | Overall Winged: Bobby Santos III
Midwestern Winged: Aaron Pierce Overall Non-Winged: Bobby Santos III Midwestern Non-Winged: Bobby Santos III Overall: Bobby Santos III |
| 2018 | Brian Gerster |
| 2017 | Jason Blonde |
| 2016 | Aaron Pierce |
| 2015 | Aaron Pierce |
| 2014 | Jason Blonde |
| 2013 | Jason Blonde |
| 2012 | Billy Tyler |
| 2011 | Jim Swain |
| 2010 | Kevin Feeney |
| 2009 | Jason Blonde |
| 2008 | Jason Blonde |
| 2007 | Jason Blonde |
| 2006 | Tom Fedewa |
| 2005 | Cameron Dodson |
| 2004 | Bill Tyler* |
| Jason Blonde* | |
| 2003 | Tom Fedewa |
| 2002 | Tim Cox |
| 2001 | Gary Fedewa |
| 2000 | Gary Fedewa |
| 1999 | Gary Fedewa |
| 1998 | Billy Tyler |
| 1997 | Billy Tyler |
| * Co Champion | |
Champions
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