| 2025 | Jeff Vukovich | Lombard Orioles | |
| 2024 | Jeff Vukovich | Lombard Orioles | |
| 2023 | Steve Elliott | West Allis Nationals | |
| 2022 | Steve Elliott | West Allis Nationals | |
| 2021 | Jeff Vukovich | Lombard Orioles | |
| 2020 | Tim Moyer | Sheboygan A's | |
| 2019 | Steve Elliott | West Allis Nationals | |
| 2018 | Jeff Vukovich | Lombard Orioles | |
| 2017 | Jeff Vukovich | Lombard Orioles | |
| 2016 | Jeff Vukovich | Lombard Orioles | |
| 2015 | Jeff Vukovich | Lombard Orioles | |
| 2014 | Tyler Martin | Sheboygan A's | |
| 2013 | Jeff Vukovich | Lombard Orioles | |
| 2012 | Jeff Vukovich | Lombard Orioles | |
| 2011 | Jeff Vukovich | Lombard Orioles | |
| 2010 | Jeff Vukovich | Lombard Orioles | |
| 2009 | Jeff Vukovich | Lombard Orioles | |
| 2008 | Jeff Vukovich | Lombard Orioles | |
| 2007 | Jeff Vukovich | Lombard Orioles | |
| 2006 | Tim Pulizzano | Kenosha Kings | |
| 2005 | Jeff Vukovich | Lombard Orioles | |
| 2004 | Jeff Vukovich | Lombard Orioles | |
| 2003 | Ron Biga | Chicago | |
| 2002 | Jeff Vukovich | Lombard Orioles | |
| 2001 | Jeff Vukovich | Lombard Orioles | |
| 2000 | Craig Kloes | Sheboygan A's | |
| 1999 | Craig Kloes | Sheboygan A's | |
| 1998 | Tom Winske | Green Bay Blue Ribbons | |
| 1997 | Dave Moyer | Sheboygan A's | |
| 1996 | Jeff Vukovich | Lombard Orioles | |
| 1995 | Dennis Ruh | Green Bay Blue Ribbons | |
| 1994 | Dennis Ruh | Green Bay Blue Ribbons | |
| 1993 | Pat Cambell | Janesville Aces | |
| 1992 | Dennis Ruh | Green Bay Blue Ribbons | |
| 1991 | Dave Moyer | Sheboygan A's | |
| 1990 | Joe Coulter | Janesville Aces | |
| 1989 | Joe Coulter | Janesville Aces | |
| 1988 | Joe Coulter | Janesville Aces | |
| 1987 | Bob Sauger | Sheboygan A's | Co-Winner |
| 1987 | Gerry Staub | Rockford Blackhawks | Co-Winner |
| 1986 | Butch Maglio | Madison Avenue Bar | |
| 1985 | Dennis Ruh | Green Bay Blue Ribbons | |
| 1984 | Sam Hamstra | Delavan | |
| 1983 | Marty Bell | Madison Avenue Bar | |
| 1982 | Marty Bell | Madison Avenue Bar | |
| 1981 | Chuck Zeichert | Sheboygan A's | |
| 1980 | Dennis Ruh | Green Bay Blue Ribbons | |
| 1979 | Boyd Rohde | Horicon | |
| 1978 | Tom Bennett | Madison Howard Johnson | |
| 1977 | Dennis Ruh | Green Bay Blue Ribbons | |
| 1976 | Dennis Ruh | Green Bay Blue Ribbons | |
| 1975 | Jerry Davis | Janesville Aces | |
| 1974 | Tom Bennett | Madison Leske |
