| Year |
|
Winner |
Former Team(s) |
| 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 |
|
