Edgartown Yacht Club Regatta
Winners of First Day
| Year | Yacht | Skipper |
| 1928-1953 | No Record | |
| 1954 | Roweida IV | Gordon Beggs |
| 1955 | Quip | Lee Hunter |
| 1956 | Hermanos | Allan L. Priddy |
| 1957 | Bettayet | Ross W. Richards |
| 1958 | Dungolphin | Durban A. McGraw |
| 1959 | Marna | John T. Fallon |
| 1960 | Marna | John T. Fallon |
| 1961 | Marna | John T. Fallon |
| 1962 | Nonchy | J.W. Scarborough, Jr. |
| 1963 | Venture | David D. Steere |
| 1964 | Marna | John T. Fallon |
| 1965 | Venture | David D. Steere |
| 1966 | Sovereign IV | Harrison P. Bridge |
| 1967 | Marna | John T. Fallon |
| 1968 | Marna | John T. Fallon |
| 1969 | Bettawin | Ross W. Richards |
| 1970 | Bettawin | Ross W. Richards |
| 1971 | No Record | |
| 1972 | Bettawin | Ross W. Richards |
| 1973 | Pertelote | Boardman Lloyd |
| 1974 | Pertelote | Francis V. Lloyd, III |
| 1975 | Pertelote | Boardman Lloyd |
| 1976 | Victura | Joseph P. Kennedy, II |
| 1977 | Cirrus | George P. Edmonds, III |
| 1978 | Invader | Lewis J.H. Gunn |
| 1979 | Invader | Lewis J.H. Gunn |
| 1980 | No Record | |
| 1981 | Madeline | Richard W. Burnes, Jr. |
| 1982 | Victura | Edward M. Kennedy, Jr. |
| 1983 | Pertelote | Francis V. Lloyd, III |
| 1984 | Cirrus | George P. Edmonds, III |
| 1985 | Cochenoe | Donald F. Law, Jr. |
| 1986 | Marna | John T. Fallon, Jr. |
| 1987 | Invader | Lewis J.H. Gunn |
| 1988 | Scarlet | Thomas H. O’Toole |
| 1989 | Scarlet | Thomas H. O’Toole |
| 1990 | Scarlet | Thomas H. O’Toole |
| 1991 | Eight Ball | Karl E. Anderson |
| 1992 | Cirrus | Alden Edmonds |
| 1993 | Molly | John T. McDonough |
John T. Fallon Trophy
Presented by the Class Association in Honor of John T. Fallon
| Year | Yacht | Skipper |
| 1994 | Touch o’ Gray | Lee S. Williams |
| 1995 | Eight Ball | Karl E. Anderson |
| 1996 | Cirrus | Holly Edmonds |
| 1997 | Eight Ball | Karl E. Anderson |
| 1998 | Rapparee | Peter L. O’Keeffe |
| 1999 | Chanzia | Lloyd M. McManus, Jr. |
| 2000 | Yankee Dime | Alden Edmonds |
| 2001 | Pieces of 8 | Karl E. Anderson |
| 2002 | Yankee Dime | B. Francis Saul |
| 2003 | Eowyn | George Largay |
| 2004 | Lindy | David McDonough |
| 2005 | Aurora | Holly Edmonds |
| 2006 | Cochenoe | John Kiley |
| 2007 | Heritage | John T. Fallon, Jr. |
| 2008 | Cochenoe | Donald F. Law, Jr. |
| 2009 | Mad Jack | Jack Hamilton |
| 2010 | Mad Jack | Jack Hamilton |
| 2011 | Mad Jack | Jack Hamilton |
| 2012 | Smoke | Richard Feeny |
| 2013 | Beltane | Jim Cunningham |
| 2014 | Heritage | John T Fallon, Jr. |
| 2015 | Smoke | Joe Lotuff |
| 2016 | Aurora | Holly Edmonds |
| 2017 | Heritage | John T Fallon, Jr. |
| 2018 | Mad Jack | Jack Hamilton |
| 2019 | Madeline | Eli and Henry Burnes |
| 2020 | Smoke | Joe Lotuff |
| 2021 | Race abandoned | |
| 2022 | Kerplunk | Kent Plunkett |
| 2023 | Aria | Peter Shope |
| 2024 | Aria | Peter Shope |
| 2025 | Patience | Ben Blum |
Winners of the Second Day
| Year | Yacht | Skipper |
| 1928-1953 | No Record | |
| 1954 | Sea Fox | Heywood Fox |
| 1955 | Bettayet | Ross W. Richards |
| 1956 | Hermanos | Allan L. Priddy |
| 1957 | Bettayet | Ross W. Richards |
| 1958 | Ebb | A. Leighton |
| 1959 | No Record | |
| 1960 | Sovereign IV | Harrison P. Bridge |
| 1961 | Ebb | George Rockwood |
| 1962 | Venture | David D. Steere |
| 1963 | Hermanos | Allan L. Priddy |
| 1964 | Marna | John T. Fallon |
| 1965 | Marna | John T. Fallon |
| 1966 | Uncle Benny | Stanley W. Moore |
| 1967 | Marna | John T. Fallon |
| 1968 | Marna | John T. Fallon |
| 1969 | Race Abandoned – Light Air | |
| 1970 | Bettawin | Ross W. Richards |
| 1971 | No Record | |
| 1972 | Marna | John T. Fallon |
| 1973 | Cirrus | George P. Edmonds, Jr. |
| 1974 | Pertelote | Francis V. Lloyd, III |
| 1975 | Pertelote | Boardman Lloyd |
| 1976 | We’re Here | Connie M. Tracy |
| 1977 | Molly | Alan T. McDonough |
| 1978 | Madeline | Richard M. Burnes, Jr. |
| 1979 | Cirrus | George P. Edmonds, Jr. |
| 1980 | Cirrus | George P. Edmonds, Jr. |
| 1981 | Molly | Alan T. McDonough |
| 1982 | Venture | David D. Steere |
| 1983 | Victura | Edward M. Kennedy, Jr. |
| 1984 | Race Not Scored | |
| 1985 | Snow Goose | Lewis J.H. Gunn |
| 1986 | Cochenoe | Donald F. Law, Jr. |
| 1987 | Victura | Edward M. Kennedy, Jr. |
| 1988 | Intuition | James H. Light |
| 1989 | Cochenoe | Donald F. Law, Jr. |
| 1990 | Eight Ball | Karl E. Anderson |
| 1991 | Lucky Lady | Bradford W. Tracy |
| 1992 | Eight Ball | Karl E. Anderson |
| 1993 | Cirrus | Holly Edmonds |
David D. Steere Trophy
Presented to the Class Association in Memory of
David D. Steere by the Steere Family
| Year | Yacht | Skipper |
| 1994 | Invader | Lewis J.H. Gunn |
| 1995 | Eight Ball | Karl E. Anderson |
| 1996 | Race cancelled – High Winds | |
| 1997 | Lente Festina | G. Kent Plunkett |
| 1998 | Cirrus | Holly Edmonds |
| 1999 | Lente Festina | G. Kent Plunkett |
| 2000 | Yankee Dime | Alden Edmonds |
| 2001 | Pieces of 8 | Karl E. Anderson |
| 2002 | Yankee Dime | B. Francis Saul, III |
| 2003 | Pieces of 8 | Todd Kittredge |
| 2004 | Pieces of 8 | Todd Kittredge |
| 2005 | Pieces of 8 | Todd Kittredge |
| 2006 | Pieces of 8 | Todd Kittredge |
| 2007 | Eowyn | George Largay |
| 2008 | Cochenoe | Donald F. Law, Jr. |
| 2009 | Eowyn | George Largay |
| 2010 | Pieces of 8 | Heather Gregg |
| 2011 | Eowyn | Tim Wadlow |
| 2012 | Smoke | Richard Feeny |
| 2013 | Beltane | Jim Cunningham |
| 2014 | Mad Jack | Jack Hamilton |
| 2015 | Mad Jack | Jack Hamilton |
| 2016 | Scout | Kelsey Wheeler |
| 2017 | Madeline | Henry Burnes |
| 2018 | Madeline | Henry Burnes |
| 2019 | Kerplunk | Kent Plunkett |
| 2020 | Scout | Fraser Pesek |
| 2021 | Smoke | Jack Howard |
| 2022 | Smoke | Clark Lotuff |
| 2023 | Not Sailed | High Winds |
| 2024 | Three Sticks | Peter McAvoy |
| 2025 | Scout | John Fallon |