(1959 - Present)
| Season | Division | Player | Team |
| 2025 | North | Tanner Galeazzi | Hustisford |
| North | Michael Seegers | Hartford | |
| South | Tyler Doyle | Lebanon | |
| 2024 | North | Tanner Galeazzi | Hustisford |
| South | KJ Banse | Rubicon | |
| 2023 | North | Sean Menzel | Kewaskum |
| South | Hunter Herpel | Lebanon | |
| 2022 | North | Jonathan Wizner | Thiensville-Mequon |
| South | Cameron Schuett | Clyman | |
| 2021 | North | Aaron Roeseler | Hustisford |
| South | Brandon Egnarski | Neosho | |
| South | Michael Knutson | Johnson Creek | |
| 2020 | North | None - COVID | |
| South | None - COVID | ||
| 2019 | North | Jared Chesak | Kewaskum |
| North | Adam Ryan | Oakfield | |
| South | Tanner Galeazzi | Hustisford | |
| 2018 | North | Griff Lukes | Hartford |
| South | Josh Oswald | Clyman | |
| 2017 | North | Aaron Roeseler | Hustisford |
| South | Dusty Jacobson | Neosho | |
| South | Brian Kushava | Madison Rockers | |
| 2016 | North | David Rosser | Hustisford |
| South | Paul Mutch | Madison Rockers | |
| 2015 | North | Mitch Beau | Brownsville |
| South | Alex Brown | Madison Rockers | |
| 2014 | North | Drew Palmer | Hartford |
| South | Dusty Jacobson | Neosho | |
| 2013 | North | James Goodfellow | Brownsville |
| South | Joe Shere | Milton | |
| 2012 | North | Jason Strobel | Kewaskum |
| South | Kyle Johnson | Janesville | |
| 2011 | North | Mike Merk | Oakfield |
| South | Charlie Hurtgen | Clyman | |
| 2010 | North | Eric Roecker | Rubicon |
| South | Dan Schauer | Clyman | |
| 2009 | North | Aaron Braund | Rubicon |
| South | Jeff Zielke | Clyman | |
| 2008 | North | Joe Hennen | Hustisford |
| South | Jason Wesemann | Clyman | |
| 2007 | North | Tyler Witkowski | Brownsville |
| South | Tim Ladron | Clyman | |
| 2006 | North | Aaron Braund | Rubicon |
| South | Kevin Schultz | Juneau | |
| 2005 | North | Aaron Braund | Rubicon |
| South | Casey Powell | Madison L.T. | |
| 2004 | North | Aaron Braund | Rubicon |
| South | Tim Ladron | Clyman | |
| 2003 | North | Shane O'Hagan | Rubicon |
| South | Brady Endl | Helenville | |
| 2002 | North | Chris Morgan | Oakfield |
| South | Brent Deremer | Madison Shoe Box | |
| 2001 | North | Josh Stoffel | Brownsville |
| South | Stanley Evans | Madison Shoe Box | |
| 2000 | North | Matt Denure | Pardeeville |
| South | Jason Wesemann | Clyman | |
| 1999 | North | Dave Berg | Rubicon |
| North | Mark Nelson | Hustisford | |
| South | Tim Mommaerts | Clyman | |
| 1998 | North | Matt Schaefer | Rubicon |
| South | Sean Smith | Ashippun | |
| 1997 | North | Scott Powell | Rubicon |
| North | Matt Denure | Pardeeville | |
| South | Scott Staude | Johnson Creek | |
| 1996 | North | Doug Gonring | Kewaskum |
| South | Jose Alba | Watertown | |
| South | Tim Wagner | Helenville | |
| 1995 | North | Mark Robel | Rubicon |
| South | Kevin Murphy | Watertown | |
| 1994 | North | Rob Michels | Slinger |
| South | Jeff Laesch | Helenville | |
| 1993 | North | Doug Gonring | Kewaskum |
| South | Jon Zirbel | Neosho | |
| 1992 | North | Craig Semler | Rubicon |
| South | Todd Evers | Clyman | |
| 1991 | North | Doug Gonring | Kewaskum |
| South | Greg Klietz | Jonson Creek | |
| 1990 | North | Todd Bonlander | Fond du Lac |
| North | Dave Geldnich | Slinger | |
| South | Kirk Kaul | Hustisford | |
| 1989 | North | Tim Bresser | Waupun |
| North | Tony Cole | Brownsville | |
| Central | Kirk Kaul | Hustisford | |
| Central | Jon Moldenhauer | Clyman | |
| South | Scott Pompe | Watertown | |
| 1988 | North | Joe Ryan | Oakfield |
| South | Craig Semler | Rubicon | |
| 1987 | North | Bill Kreuser | Slinger |
| South | Jon Zirbel | Horicon | |
| 1986 | North | Gary Ryan | Oakfield |
| South | Kirk Kaul | Hustisford | |
| 1985 | North | Mike Urban | Oakfield |
| South | Steve Lehman | Juneau | |
| 1984 | North | Mike Zimmerman | Oakfield |
| South | Dale Nehls | Hustisford | |
| 1983 | North | Larry Held | Slinger |
| South | Jim Braunschweig | Johnson Creek | |
| 1982 | North | Mike Zimmerman | Oakfield |
| South | Gary Will | Hustisford | |
| 1981 | North | Mike Urban | Oakfield |
| North | Tom Salmon | Slinger | |
| South | Kirk Kaul | Hustisford | |
| 1980 | North | Jack Held | Slinger |
| North | Chris Ogle | Oakfield | |
| South | Gary Wild | Juneau | |
| 1979 | North | Rick Bloohm | Brownsville |
| South | Ed Edwards | Lebanon | |
| 1978 | North | Greg Collien | Oakfield |
| South | Lynn Held | Lebanon | |
| 1977 | North | Bart Bruins | Waupun |
| South | Kirk Kaul | Hustisford | |
| 1976 | North | Tom Walsh | Long Lake |
| South | Fred Eddy | Juneau | |
| 1975 | North | Fritz Goebel | Long Lake |
| South | Jim Hoppe | Lebanon | |
| 1974 | North | Bud Kollmansberger | Mayville |
| South | Don Held | Lebanon | |
| 1973 | North | Jim Gantner | Long Lake |
| South | Rick Held | Slinger | |
| 1972 | North | Mike Haberkorn | Oakfield |
| South | Gary Schwefel | Lebanon | |
| South | Dan Hinzmann | Johnson Creek | |
| 1971 | North | Mark Rohde | Horicon |
| South | Al Alt | Hustisford | |
| 1970 | North | Duan Gourlie | LeRoy |
| South | Jim Pirkel | Watertown | |
| 1969 | North | Larry Schaefer | Oakfield |
| South | Gary Schwefel | Lebanon | |
| 1968 | North | Paul Christian | Mayville |
| South | Larry Held | Hustisford | |
| 1967 | North | Hugh Roberts | Randolph |
| South | Lou Keller | Ashippun | |
| 1966 | North | Robert Messner | Oakfield |
| South | Steve Ellsworth | Johnson Creek | |
| 1965 | North | Dean Wilderman | Mayville |
| South | Don Christopherson | Ashippun | |
| 1964 | North | Terry Nenno | Randolph |
| South | Gary Schlieve | Ashippun | |
| 1963 | Emil Gove | Randolph | |
| 1962 | Chuck Erdman Jr | Rubicon | |
| 1961 | George Held | Hustisford | |
| 1960 | Dean Wilderman | Mayville | |
| 1959 | Fran Hofmaier | Slinger |