| 2026 | Thomas Burton | Bruce Martinson, Andy Ferguson, Max Sigel | M-9 | |
| 2025 | Kyle Navin | Dave Navin, Quin Frazier, Norman Berge | | |
| 2024 | Eddie Cox | Coye Harrett, Paris Henken, Ed Cox | | |
| 2023 | Tom Burton | Bruce Martinson, Andy Ferguson | | |
| 2022 | Vincent Porter | Tony Jewett, Chapman Petersen, Hannah Lee Noll | | |
| 2021 | Harry Melges IV | Finn Rowe, Ripley Shelley, Severin Gramm | | |
| 2020 | Harry Melges IV | Kyle Navin, Finn Rowe, Ripley Shelley | | |
| 2019 | Brian Porter | RJ Porter, Colin Rowe | | |
| 2018 | Vincent Porter | Coye Harrett, Clifford Porter, Addy Ferguson | | |
| 2017 | Harry Melges IV | Finn Rowe, Jeremy Wilmot, Patrick Wilson | | |
| 2016 | Brian Porter | RJ Porter, Annie Rowe, Colin Rowe | | |
| 2015 | Jeff Bonanni | Mike O'Brian, Mathew Goetting, Maggie Condon | | |
| 2014 | Sam Rogers | Chrisy Hughes, Tony Jewett, Lynn Jewett | | |
| 2013 | Kevin Jewett | Jim Campbell, David Buckley, Carolina Jewett | | |
| 2012 | Andy Burdick | Toby Sutherland, Jim Gluek, Deb Ziegler | | |
| 2011 | Chris Jewett | Pat Hughes, Rick Kotovic | | |
| 2010 | Peter Hurley | Glen Dickson, Park Benjamin | | |
| 2009 | Tom Burton | Andy Ferguson, Bruce Martinson | | |
| 2008 | Andy Burdick | Peter Keck, Coye Harrett, Lindsay Bartel | | |
| 2007 | Sam Rogers | Zak Franberg, Bill Freytag | | |
| 2006 | Brian Porter | Dave Navin, Charlie Harrett | | |
| 2005 | Brian Porter | Dave Navin, Charlie Harrett | | |
| 2004 | Brian Porter | Dave Navin, Charlie Harrett | | |
| 2003 | Sheldon Ecklund | Hans Melges, Harry Melges III | | |
| 2002 | Mike Darrow | Brian Jones, Rick Kotovic, Kathy Gutenkunst | | |
| 2001 | Bob Biwer | August Barkow, David Buckley, Robin Dale | | |
| 2000 | Andy Burdick | Peter Keck, Jeff Ecklund | | |
| 1999 | Brian Porter | John Porter, Bill Freytag, Brian Allen | | |
| 1998 | Harry Melges III | Bill Freytag, Jeff Ecklund, Katy Hanny | | |
| 1997 | Brian Porter | John Porter, Bill Freytag | | |
| 1996 | Andy Burdick | Harry Melges, Jeff Ecklund, Vincent Porter | | |
| 1995 | Brian Porter | John Porter, Billy Freytag | | |
| 1994 | Dave Magno | JJ Applegate, James Maida, Leah Wagner | | |
| 1993 | Andy Burdick | Harry Melges III, Candace Burdick, Peter Keck | | |
| 1992 | Harry Melges III | Hans Melges, Suzanne Melges, Judd Hirschberg | | |
| 1991 | Tom Burton | Bruce Martinson, Tim Regan, Chrissy Barnett | | |
| 1990 | Harry Melges III | Hans Melges, Judd Hirschberg, Suzanne Kelsey | | |
| 1989 | Harry Melges III | Hans Melges, Judd Hirschberg, Suzanne Kelsey | | |
| 1988 | Harry Melges III | Hans Melges, Judd Hirschberg, Jason Hirschberg | | |
| 1987 | Harry Melges III | Hans Melges, Jim Gluek, Angie Sheahan | | |
| 1986 | Harry Melges III | Hans Melges, Jim Gluek, Mike Sigel | | |
| 1985 | Scott Callahan | Bob Koar, Paul Egee, Jenny Adams | | |
| 1984 | Brian Porter | John Porter, Tom Freytag | | |
| 1983 | Buddy Melges | Hans Melges, Harry Melges III, David Wall | | |
| 1982 | Bill Allen | Judd Hirschberg, Charlie Harrett, Susie Allen | | |
| 1981 | Bill Campbell | Russ Lines, Glenn Lines, Sherri Campbell | | |
| 1980 | Willie De Camp | Peter Van Duyne, Nick Post, Doug Vreeland | | |
| 1979 | Buddy Melges | Harry Melges III, William Bentsen, Scott Ripkey | | |
| 1978 | Buddy Melges | Bob Penticoff, Tim O'Keefe | | |
| 1977 | Gordon Bowers | Mark Bowers, Steve Schmidt, David Schmidt | | |
| 1976 | Gordon Bowers | Mark Bowers, Steve Schmidt, David Schmidt | | |
| 1975 | Bill Allen | Kay Larkin, Ron Frankel, Brian Porter | | |
| 1974 | Bill Allen | Cathy Ward, Dick Allen, Ron Frankel | | |
| 1973 | Bill Allen | Heidi Huck, Dick Allen, Ron Frankel | | |
| 1972 | Harold Allen | Westley Crawford, Gordy Bowers, Dick Allen | | |
| 1971 | Brad Robinson | John Gluek, Steve Schmidt, HM Baskerville III | | |
| 1970 | Bill Allen | Bob Allen, Dick Allen, HM Baskerville III | | |
| 1969 | Buddy Melges | Thomas Szymanski, Kay Larkin, Bill Matson | | |
| 1968 | Brad Robinson | Alan Jackman, Buckley Ives, Richard Tracy | | |
| 1967 | Brad Robinson | Gordy Bowers, Jeannie Bowers, Chuck Gorgen | | |
| 1966 | Runyon Colie | Tom Weldon, John Dughi, Ray Laffin | | |
| 1965 | Buddy Melges | Walter Larkin, Serge Graz, Brad Harvey | | |
| 1964 | Bill Grunow | John Porter, Bill Freytag, Brian Allen | | |
| 1963 | Gordon Lindemann | Anne Lindemann, Robert Norton | | |
| 1962 | Gordon Lindemann | Anne Lindemann, Robert Norton | | |
| 1961 | Nat Robbins | Mary Robbins, Sally Hurd, Cecil Hurd Jr | | |