| 2023 | Brian Lacy | 2023 | Tie - Dale Schmitz, Gerry Angers, John Wright | 2023 | Molino/Ferguson | |
| 2022 | Will-I-Am Fergi-son | 2022 | Shaun Rubin | 2022 | Molino/Ferguson | |
| 2021 | RAK | 2021 | Sean "the Weatherman" Nolan / RAK | 2021 | Runningbach + Hokie Pokie | |
| 2020 | Covid - Cancelled | 2020 | Covid - Cancelled | 2020 | Covid - Cancelled | |
| 2019 | Matt 'Mr. Cub' Lawson | 2019 | Collingsworth/Provin | 2019 | Molino/Ferguson | |
| 2018 | Cullen 'Linebacher' Rombach | 2018 | Richard (Brewster) Preuster | | | |
| 2017 | Kyla 'Brady Back Ribs' Rakoczy | 2017 | Dale 'Schlitz' Schmitz | | | |
| 2016 | Steve 'Perry' Reed | 2016 | Dale 'Schlitz' Schmitz | | | |
| 2015 | Danny 'Steel Curtain' Molino | 2015 | Jimbo O'Sullivan - Kyle Brett | | | |
| 2014 | RAK | 2014 | Sean "the Weatherman" Nolan | | | |
| 2013 | Matt 'Mr. Cub' Lawson | 2013 | Jimbo O'Sullivan - Kyle Brett | | | |
| 2012 | Kyla 'KSWAG' Rakoczy | 2012 | Dale 'Schlitz' Schmitz | | | |
| 2011 | Bob 'Call me George' Brett | 2011 | Joel 'Christmas' Noel | | | |
| 2010 | Mr. Ed' Schmitz | 2010 | Bob Brett | | | |
| 2009 | Collingsworth | 2009 | 3 Way Tie | | | |
| 2008 | Robert 'Old Man' Nolan | 2008 | Patrick Noel | | | |
| 2007 | Collingsworth | 2007 | Tie - 4 ways | | | |
| 2006 | Chris Rakoczy | 2006 | Tie - The Bretts - Ed, Edd, n, Eddy | | | |
| 2005 | Dale Schmitz | 2005 | Robert Nolan - Jeff "Weasel" Fink | | | |
| 2004 | Dale Schmitz | 2004 | Sean "the Weatherman" Nolan | | | |
| 2003 | Dale Schmitz | 2003 | Jimmy Weir | | | |
| 2002 | Collingsworth | 2002 | Harry Sirione | | | |
| 2001 | RAK | 2001 | Jeff Fink | | | |
| 2000 | Craig Monnell | 2000 | Jeff Fink | | | |
| 1999 | Sean Nolan - Jeff Deren | 1999 | Chris Rakoczy | | | |
| 1998 | Juan Hubbard | 1998 | John Wright - Suzanne Rakoczy | | | |
| 1997 | Mark Ludwigsen | 1997 | GE Capital Modular Space | | | |
