| Year |
Winner |
Former Team(s) |
| 2024 |
Wes Braunschweig |
Neosho, Ashippun, Clyman |
| 2023 |
Ross Roeseler |
Hustisford |
| 2022 |
Tim Fitzsimmons |
Clyman |
| 2021 |
Dave Zimmerman |
Slinger, Pardeeville |
| 2020 |
None Selected - COVID |
|
| 2019 |
Gary Schwefel |
Lebanon |
| 2018 |
Steve Salter |
Slinger |
| 2017 |
Lynn Held |
Lebanon, Hustisford |
| 2016 |
Phil Nehls |
Hustisford, Clyman, Rubicon |
| 2015 |
Steve Lehman |
Juneau, Clyman |
| 2014 |
Neal Kohlhoff |
Clyman |
| 2013 |
Ken Held |
Neosho, Slinger |
| 2012 |
Bill Bergin |
Lebanon |
| 2011 |
Don Christopherson |
Ashippun |
| 2010 |
None Selected |
|
| 2009 |
Hugh Roberts |
Randolph |
| 2008 |
Jim Pirkel |
Watertown |
| 2007 |
Jim Braunschweig |
Johnson Creek |
| 2006 |
Don Held |
Rubicon, Hustisford, Lebanon |
| 2005 |
Gib Youngbeck |
Mayville |
| 2004 |
Rich Block |
Watertown |
| 2003 |
Bob Kuehl |
Hustisford |
| 2002 |
Will Eske |
Lebanon |
| 2001 |
Howard "Sam" Narges |
Long Lake |
| 2000 |
Fran Hofmaier |
Slinger |
| 1999 |
Carl Heimerl |
Rubicon |
| 1998 |
Bud Bellon |
Former Commissioner, RR Old-Timers Secretary |
| 1997 |
L.O. "Ozzie" Bloohm |
Brownsville |
| 1996 |
Elmer Marks |
Former Commissioner, Hustisford, Ashippun |
| 1995 |
Norm "Lefty" Bischoff |
Juneau |
|
