(1984 - Present)
| Year | Winner | Former Team(s) | |
| 2025 | None Selected | ||
| 2024 | None Selected | ||
| 2023 | None Selected | ||
| 2022 | None Selected | ||
| 2021 | None Selected | ||
| 2020 | None Selected | ||
| 2019 | None Selected | ||
| 2018 | None Selected | ||
| 2017 | None Selected | ||
| 2016 | Ken "Patz" Lerch | Brownsville | |
| 2015 | Peter Kuehl | Hustisford | |
| 2014 | Mitch Hackbarth | Hustisford | |
| 2013 | Ken Kluck | Hartford | |
| 2012 | None Selected | ||
| 2011 | Stony Steinbach | Mayville | |
| 2010 | Lance Pirkel | Watertown, Helenville | |
| 2009 | Frank "Dropsey" Sorgent | Mayville | |
| 2008 | None Selected | ||
| 2007 | None Selected | ||
| 2006 | Earl Dewitz | Waupun, Oakfield | |
| 2005 | Mike Strey | Lebanon | |
| 2004 | Harriet Kaul | Hustisford | |
| 2003 | Smokey Wendorf | N/A | |
| 2002 | Howie Stallman | Watertown, Johnson Creek | |
| 2001 | Herb Schlieve | Waupun | |
| 2000 | Chappy Chapman | Ashippun | |
| 1999 | Speedy Threde | N/A | |
| 1998 | Harold "Bud" Allerman | Watertown | |
| 1997 | Eddie Broombaugh | Horicon | |
| 1996 | Alvin "Carp" Reinhard | N/A | |
| 1995 | Fritz Wondra | Long Lake, Campbellsport | |
| 1994 | Ron Quandt | Rubicon | |
| 1993 | Lou Pluim | Waupun | |
| 1992 | Erv Buchert | Watertown, Umpire | |
| 1991 | Augie Bischoff | Juneau, League Commissioner | |
| 1990 | Ray Schilling | Horicon | |
| 1989 | Herb Jeche | Hustisford | |
| 1988 | Ernie Schramm | Lebanon | |
| 1987 | Mike Ries | Brownsville | |
| 1986 | Elmer Hackbarth | Lebanon | |
| 1985 | Bob Mullen | Long Lake | |
| 1984 | Harry Schramm | Lebanon |