| Season | Helm | Crew | Boat | Venue |
|---|---|---|---|---|
| 2010 | John Applegate | |||
| 2009 | Sunny Sawyer * | Baleno | ||
| 2009 (2nd) | Paul Reinicke | Helen Rehberger | V-151 | |
| 2009 (3rd) | Maggie Walsh | V-76 | ||
| 2008 | Jan Gill | Debbie Gill | WL111 Riff Raff | |
| 2007 | John Applegate | |||
| 2006 | Paul Reinicke | Hunter | ||
| 2005 | Jan Gill | Riff Raff | ||
| 2004 | Lauren von Bereghy | |||
| 2003 | Courtney Krejci | Tight Ship | ||
| 2002 | Kara Kaiser | Nein Nein | ||
| 2001 | Paul Reinicke | Hunter | ||
| 2000 | Eric Hood | Doxa | ||
| 1999 | Andy Burdick | Team 45 | ||
| 1998 | Dixon Tews | In Tune | ||
| 1997 | Jim Barkow | Flash | ||
| 1996 | David Strothman | Strange Brew | ||
| 1995 | Jim Gluek | Kingfisher | ||
| 1994 | Jane Pegel | Calamity Jane | ||
| 1993 | Kevin Jewett | Magic | ||
| 1992 | Rob Conley | Fahrvergcrusin | ||
| 1991 | Chris Jewett | Fire Brand | ||
| 1990 | Jane Pegel | Calamity Jane | ||
| 1989 | John Dennis | Puffer VI | ||
| 1988 | Andy Burdick | Stormin' | ||
| 1987 | Garry Winter | FTASB | ||
| 1986 | Andy Burdick | Stormin' | ||
| 1985 | John Dennis | Puffer V | ||
| 1984 | John Dennis | Puffer V | ||
| 1983 | Harry Melges III | Whistler | ||
| 1982 | Harry Melges III | Whistler | ||
| 1981 | Mark Christensen | Madness | ||
| 1980 | Scott Hudson | TRUE Blue | ||
| 1979 | Susan Pegel | Stormy V | ||
| 1978 | Tom Burton | Vendetta | ||
| 1977 | Bob Nuffort | Yahoo | ||
| 1976 | Bob Nuffort | Yahoo | ||
| 1975 | Bob Nuffort | Yahoo | ||
| 1974 | Henry Bossett | Sassy | ||
| 1973 | Andy Schoettle | Scat | ||
| 1972 | Jane Pegel | Calamity Jane XII | ||
| 1971 | Dave Ferguson | Dauntless | ||
| 1970 | Jane Pegel | Calamity Jane XII | ||
| 1969 | Jane Pegel | Calamity Jane XII | ||
| 1968 | Robert Jones | Gambit | ||
| 1967 | Jane Pegel | Calamity Jane XII | ||
| 1966 | Ed Smith | Cat's Paw | ||
| 1965 | Jane Pegel | Calamity Jane XII | ||
| 1964 | Ed Smith | Cat's Paw | ||
| 1963 | Jane Pegel | Calamity Jane X | ||
| 1962 | Jane Pegel | Calamity Jane X | ||
| 1961 | Jane Pegel | Calamity Jane | ||
| 1960 | Jane Pegel | Calamity Jane | ||
| 1959 | Fritz Kroeger | Brotherly Luff |
Sources: d282wvk2qi4wzk.cloudfront.net, web.archive.org. A * marks a note (hover): a correction to the published roll, or where a title came from.
Honour rolls list titles, not results, so they do not feed the ratings. A name links to a sailor profile only where the match is clear.