| Mike Morrissey & Joe Eppstein | 1976 | M-20 | Lake Mendota |
| Tom reps & Kit Tily | 1986 | M-20 | Lake Mendota |
| Karl Matzke & Jill Schmidt | 1989 | M-20 | Pewaukee Lake |
| Tom Reps & Nancy Hall | 1990 | M-20 | Lake Minnetonka |
| Tom Reps & Nancy Hall | 1991 | M-20 | Lake Mendota |
| Tom Reps & Fran Wong | 1992 | M-20 | Lake Geneva |
| Tom Reps & Fran Wong | 1993 | M-20 | Neenah-Nodaway |
| Karl & Jill Matzke | 1994 | M-20 | Lake Mendota |
| Tom Reps & Greg Simon | 1998 | M-20 | Lake Mendota |
| Steve Yost | 1998 | I-20 | Castle Rock Lake |
| John Hayashi | 1999 | I-20 | Lake Du Bay |
| Tom Reps | 1999 | M-20 | Lake Minnetonka |
| John Spargo & Jim Brust | 2001 | I-20 | Indian Lake, OH |
| John Spargo & Jim Brust | 2002 | I-20 | Cedar Lake, IN |
| John Spargo & Jim Brust | 2004 | I-20 | Indian Lake, OH |
| Grant Frautschi & Carolyn Curry | 2005 | I-20 | Fond du lac |
| Steve Scheck & Leigh Leonard | 2008 | I-20 | Green Lake |
| Steve Scheck & Leigh Leonard | 2009 | I-20 | Wawasee, IN |
| Stefan Schmidt | 2012 | MC/GM* | White Lake |
GM*, Grand Master (sixty years and older)
| M. E. Manchester | 1948 | C | Oshkosh |
| Ed Eloranta & Jim Bradley | 1975 | M-20 | Lake Mendota |
| Tom Reps & Mike Bottum | 1987 | M-20 | Lake Mendota |
| Tom Reps & Dan Mather | 1988 | M-20 | Lake Geneva |
| Karl Matzke & Jill Schmidt | 1989 | M-20 | Green Lake |
| Dierk Polzin & Mark Lepke | 1990 | M-20 | Oshkosh |
| Tom Reps & Mike Bottum | 1992 | M-20 | Green Lake |
| Karl & Jill Matzke | 1993 | M-20 | Lake Mendota |
| Steve Yost & Scott Noles | 2001 | I-20 | Lake Minnetonka |
| Steve Scheck & Leigh Leonard | 2003 | I-20 | Lake Mendota |
| Emily Green | 2004 | I-20 | Green Lake |
| Emily Green | 2006 | I-20 | Lake Geneva |
| Steve Scheck & Leigh Leonard | 2009 | I-20 | Green Lake |
| Stefan Schmidt | 2011 | MC/GM* | Lake Minnetonka |
| Stefan Schmidt | 2013 | MC/GM* | Okoboji |
| Meta Simon | 2014 | Opti | Girls' Championship |
| Fritz Simon | 2014 | Opti | White Fleet Championship |
GM*, Grand Master (sixty years and older)