| Season | Helm | Crew | Boat | Venue |
|---|---|---|---|---|
| 2025 | Will Utz | Will.I.am | ||
| 2024 | Oliver Gray | Chunky Monkey | ||
| 2023 | Owen Kohut | SEND IT | ||
| 2022 | Owen Kohut | SEND IT | ||
| 2021 | Kamron Kaiser | Peter Goggins | Goofball | |
| 2020 | Charlie Allen | Will Utz, Adam Biwer | Chuckwagon | |
| 2019 | Ellie Harned | Austin Steiner | Windhover | |
| 2018 | Chapman Petersen | Jack Plummer | ALL-In | |
| 2017 | Nathan Hetzler | Graham Hetzler | Penguin | |
| 2016 | Christian Spencer | Route 66 | ||
| 2015 | JP Friend | Peeps | ||
| 2014 | Kate Cox | Twizzler | ||
| 2013 | Will Huerth | Ghetto Fast | ||
| 2012 | Jack Bitney | Studfish | ||
| 2011 | Will Crary | No Xcuses | ||
| 2009 | Kate Klement | Klementine VII | ||
| 2008 | Davis Porter | Full Throttle | ||
| 2007 | Chris Banholzer | Buckshot | ||
| 2006 | Joe Kutschenreuter | Kingfisher | ||
| 2005 | Erik Bowers | Flying Toaster | ||
| 2004 | Patrick Doran | Backdraft | ||
| 2003 | Zach Hester | X-1 | ||
| 2002 | Daniel Thompson | Wind Master V | ||
| 2001 | Andrew Keane | Inside the Ride | ||
| 2000 | Andy Labanauskas | Defender | ||
| 1999 | David Blanchard | The Blur | ||
| 1998 | Vincent Porter | Wide Open | ||
| 1997 | Jesse Cote | Time “X” | ||
| 1996 | Thomas Zanios | The Edge | ||
| 1995 | Justin Hood | Zenda Express | ||
| 1994 | Brian Wynne | Road Kill | ||
| 1993 | Peter Strothman | Auf Bald | ||
| 1992 | Rob Eckert | The Last X-Cuse | ||
| 1991 | Jim Barkow | Tactics | ||
| 1990 | Chris Jewett | X-Cel | ||
| 1989 | Bill Lieber | Wild Willy | ||
| 1988 | Joe Curtes | Go “4” It | ||
| 1987 | Dan Keck | No Pain-No Gain | ||
| 1986 | Dan Keck | Charlie's Angels | ||
| 1985 | Chad Kilander | Oh Brother! | ||
| 1984 | Scott Dale | ELAD | ||
| 1983 | Andy Burdick | Stormin' | ||
| 1982 | Andy Burdick | Stormin' | ||
| 1981 | Hans Melges | |||
| 1980 | Ed Eckert | Lucky Eddie | ||
| 1979 | Bob Frentzel | Buoy Banger | ||
| 1978 | Dean Pok | Poky | ||
| 1977 | Chip Darrow | Chipahoy | ||
| 1976 | Scott Hudson | Can't Be B-Ten | ||
| 1975 | Mary Allen Brigden | Snark III | ||
| 1974 | Jeff Hudson | Cutty Sark II | ||
| 1973 | Steve Pfeil | We-ketch-um | ||
| 1972 | Tom Burton | “X” Plorer | ||
| 1971 | John Crawford | Westerly | ||
| 1970 | David Gluek | G.J.D. | ||
| 1969 | David Ferguson | Dauntless III | ||
| 1968 | David Ferguson | Dauntless III | ||
| 1967 | Bob Nuffort, Jr. | Nuff's Luff | ||
| 1966 | Will Norris | Mom's Mink | ||
| 1965 | Eric Sternkopf | Nautilus | ||
| 1964 | Eric Sternkopf | Nautilus | ||
| 1963 | Doug Cameron | Mighty High II | ||
| 1962 | Hans Meyer | Breathrough | ||
| 1961 | Jerry McCabe | Father's Folly | ||
| 1960 | Ricky Frank | We Try Too | ||
| 1959 | Jeff Erwin | Topsy Turvy | ||
| 1958 | Ricky Frank | We Try Too | ||
| 1957 | Tom Bauman | Huff'n Puff | ||
| 1956 | Karen Kutchera * | Two Sisters | ||
| 1955 | Chuck Anderson | Invictus | ||
| 1954 | Fritz Kroeger | My Allowance | ||
| 1953 | John Anderson * | Mutineer | ||
| 1953 (2nd) | Robert Holman | Gustie | ||
| 1953 (3rd) | Timmy Brackett | Blue Heron | ||
| 1953 (3rd) | Mike Flanagan | Ak-Sar-Ben | ||
| 1953 (3rd) | Judy Best | Choppy | ||
| 1952 | Robert Holman * | Gustie | ||
| 1952 (2nd) | Pat Harring | Pickled Harring | ||
| 1952 (3rd) | John Anderson | Us Too | ||
| 1951 | Tom Ferris | Tow Head | ||
| 1950 | John S. Brackett | Ida Too | ||
| 1949 | Carol Gallun | Ripple | ||
| 1948 | Jane Wiswell | Calamity Jane | ||
| 1947 | Dave Ratcliff | Oriole | ||
| 1946 | Jim Strong | Bottoms Up II | ||
| 1942 | Bud Wallen | Cracker Jack | ||
| 1941 | W.L. Wallen, Jr. | Cracker Jack | ||
| 1940 | T.W. Norris, Jr. | Bold Venture |
Sources: d282wvk2qi4wzk.cloudfront.net, archive.org, 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.