Frederic F. Scudder Memorial Trophy
Class Championship Series, First Overall
| Year | Yacht | Skipper |
| 1949 | No Name | Benjamin Baxter |
| 1950 | No Name | Benjamin Baxter |
| 1951 | Blue Boy III | Gardner Schirmer |
| 1952 | No Name | Benjamin Baxter |
| 1953 | Mimi | W.R. Sinclair |
| 1954 | Bettayet | Ross W. Richards |
| 1955 | Hurricane – Trophy Not Awarded | |
| 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 | Venture | David D. Steere |
| 1962 | Uncle Benny | Stanley W. Moore |
| 1963 | Venture | David D. Steere |
| 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 | Bettawin | Ross W. Richards |
| 1970 | Marna | John T. Fallon |
| 1971 | Cirrus | George P. Edmonds, Jr. |
| 1972 | Venture | David D. Steere |
| 1973 | Cirrus | George P. Edmonds, Jr. |
| 1974 | Marna | John T. Fallon |
| 1975 | Pertelote | Boardman Lloyd |
| 1976 | Marna | John T. Fallon |
| 1977 | Stanley Steamer | Stanley W. Moore |
| 1978 | Invader | Lewis J.H. Gunn |
| 1979 | Invader | Lewis J.H. Gunn |
| 1980 | Invader | Lewis J.H. Gunn |
| 1981 | Lucky Lady | Bradford W. Tracy |
| 1982 | Pertelote | Boardman Lloyd |
| 1983 | Pertelote | Francis V. Lloyd, III |
| 1984 | Cochenoe | Donald F. Law, Jr. |
| 1985 | Cochenoe | Donald F. Law, Jr. |
| 1986 | Cochenoe | Donald F. Law, Jr. |
| 1987 | Cochenoe | Donald F. Law, Jr. |
| 1988 | Scarlet | Thomas H. O’Toole |
| 1989 | Cochenoe | Donald F. Law, Jr. |
| 1990 | Eight Ball | Karl E. Anderson |
| 1991 | Marna | John T. Fallon, Jr. |
| 1992 | Cirrus | Alden Edmonds |
| 1993 | Cochenoe | Donald F. Law, Jr. |
| 1994 | Eight Ball | Karl E. Anderson |
| 1995 | Marna | John T. Fallon, Jr. |
| 1996 | Cochenoe | Andrew Pesek |
| 1997 | Marna | John T. Fallon, Jr. |
| 1998 | Rapparee | Peter L. O’Keeffe |
| 1999 | Scarlet | Burt McManus |
| 2000 | Yankee Dime | Alden Edmonds |
| 2001 | Pieces of 8 | Karl E. Anderson |
| 2002 | Yankee Dime | B. Francis Saul, III |
| 2003 | Pieces of 8 | Karl E. Anderson |
| 2004 | Pieces of 8 | Todd Kittredge |
| 2005 | Aurora | Holly Edmonds |
| 2006 | Pieces of 8 | Todd Kittredge |
| 2007 | Yankee Dime | B. Francis Saul III |
| 2008 | Cochenoe | Donald F. Law, Jr. |
| 2009 | Mad Jack | Jack Hamilton |
| 2010 | Smoke | B. Francis Saul, III |
| 2011 | Pieces of 8 | Heather Gregg |
| 2012 | Smoke | Richard Feeny |
| 2013 | Beltane | Jim Cunningham |
| 2014 | Madeline | Gordon Burnes |
| 2015 | Heritage | John T Fallon, Jr |
| 2016 | Scout | Kelsey Wheeler |
| 2017 | Kerplunk | Kent Plunkett |
| 2018 | Mad Jack | Jack Hamilton |
| 2019 | Madeline | Eli and Henry Burnes |
| 2020 | Pandemic – Trophy Not Awarded | |
| 2021 | Kerplunk | Kent Plunkett |
| 2022 | Kerplunk | Kent Plunkett |
| 2023 | Aria | Peter Shope |
| 2024 | Aria | Peter Shope |
H. Manley Crosby Memorial Trophy
Class Championship Series, Second Overall
| Year | Yacht | Skipper |
| 1960 | Venture | David D. Steere |
| 1961 | Marna | John T. Fallon |
| 1962 | Venture | David D. Steere |
| 1963 | Marna | John T. Fallon |
| 1964 | Venture | David D. Steere |
| 1965 | Venture | David D. Steere |
| 1966 | Victura | Edward M. Kennedy |
| 1967 | Phebe | Robert T. Gill |
| 1968 | Cirrus | George P. Edmonds, Jr. |
| 1969 | Uncle Benny | Stanley W. Moore |
| 1970 | Bettawin | Ross W. Richards |
| 1971 | Pertelote | Malcolm Lloyd |
| 1972 | Marna | John T. Fallon |
| 1973 | Pertelote | Boardman Lloyd |
| 1974 | Pertelote | Francis V. Lloyd, III |
| 1975 | Marna | John T. Fallon |
| 1976 | Victura | Joseph P. Kennedy, II |
| 1977 | Relentless | Jeffrey Hurst |
| 1978 | Sovereign V | Harrison P. Bridge |
| 1979 | Cirrus | George P. Edmonds, Jr. |
| 1980 | Molly | Alan T. McDonough |
| 1981 | Marna | John T. Fallon |
| 1982 | Lucky Lady | Bradford W. Tracy |
| 1983 | Cochenoe | Donald F. Law, Jr. |
| 1984 | Marna | John T. Fallon |
| 1985 | Snow Goose | Lewis J.H. Gunn |
| 1986 | Marna | John T. Fallon |
| 1987 | Scarlet | Thomas H. O’Toole |
| 1988 | Cochenoe | Donald F. Law, Jr. |
| 1989 | Eight Ball | Karl E. Anderson |
| 1990 | Invader | Lewis J.H. Gunn |
| 1991 | Cochenoe | Kevin C. Cain |
| 1992 | Eight Ball | Karl E. Anderson |
| 1993 | Cirrus | Holly Edmonds |
| 1994 | Cochenoe | Sara Molyneaux |
| 1995 | Eight Ball | Karl E. Anderson |
| 1996 | Cirrus | Holly Edmonds |
| 1997 | Eight Ball | Karl E. Anderson |
| 1998 | Invader | Lewis J.H. Gunn |
| 1999 | Eight Ball | Karl E. Anderson |
| 2000 | Scarlet | Burt McManus |
| 2001 | Yankee Dime | Gordon Burnes |
| 2002 | Lente Festina | G. Kent Plunkett |
| 2003 | Lente Festina | G. Kent Plunkett |
| 2004 | Eowyn | George Largay |
| 2005 | Dauntless | Jeffrey Tracy |
| 2006 | Heritage | John T. Fallon, Jr. |
| 2007 | Mad Jack | Jack Hamilton |
| 2008 | Heritage | John T. Fallon, Jr. |
| 2009 | Eowyn | George Largay |
| 2010 | Pieces of 8 | Heather Gregg |
| 2011 | Eowyn | Tim Wadlow |
| 2012 | Beltane | Jim Cunningham |
| 2013 | Madeline | Gordon Burnes |
| 2014 | Heritage | John T Fallon, Jr. |
| 2015 | Mad Jack | Jack Hamilton |
| 2016 | Mad Jack | Jack Hamilton |
| 2017 | Scout | Sophie Pesek |
| 2018 | Kerplunk | Kent Plunkett |
| 2019 | Kerplunk | Kent Plunkett |
| 2020 | Pandemic – Trophy Not Awarded | |
| 2021 | Mad Jack | Jack Hamilton |
| 2022 | Scout | Fraser Pesek |
| 2023 | Scout | Fraser Pesek |
| 2024 | Scout | Fraser Pesek |
Ross W. Richards Memorial Trophy
Class Championship Series, Third Overall
| Year | Yacht | Skipper |
| 1973 | Invader | Lewis J.H. Gunn |
| 1974 | Cirrus | George P. Edmonds, Jr. |
| 1975 | No Name | Arthur R. Greene, Jr. |
| 1976 | We’re Here | Connie M. Tracy |
| 1977 | Cirrus | George P. Edmonds, III |
| 1978 | Relentless | Jeffrey Hurst |
| 1979 | Pertelote | Boardman Lloyd |
| 1980 | Madeline | Richard M. Burnes, Jr. |
| 1981 | Invader | Lewis J.H. Gunn |
| 1982 | Marna | John T. Fallon |
| 1983 | Cirrus | George P. Edmonds, Jr. |
| 1984 | Steamer | Thomas H. O’Toole |
| 1985 | Pertelote | Malcolm Lloyd |
| 1986 | Molly | Alan T. McDonough |
| 1987 | Invader | Lewis J.H. Gunn |
| 1988 | Molly | Alan T. McDonough |
| 1989 | Marna | John T. Fallon, Jr. |
| 1990 | Scarlet | Thomas H. O’Toole |
| 1991 | Eight Ball | Karl E. Anderson |
| 1992 | Cochenoe | Andrew Pesek |
| 1993 | Althea | Richard M. Burnes, Jr. |
| 1994 | Molly | John T. McDonough |
| 1995 | Cochenoe | Kevin C. Cain |
| 1996 | Eight Ball | Ian McNiece |
| 1997 | Sea Lyon | Charles M. Lyons |
| 1998 | Scarlet | Jean O. McManus |
| 1999 | Lente Festina | G. Kent Plunkett |
| 2000 | Cirrus | Holly Edmonds |
| 2001 | Lente Festina | G. Kent Plunkett |
| 2002 | Pieces of 8 | Karl Anderson |
| 2003 | Rapparee | Peter L. O’Keeffe |
| 2004 | Aurora | Holly Edmonds |
| 2005 | Pieces of Eight | Todd Kittredge |
| 2006 | Dauntless | Jeffrey Tracy |
| 2007 | Heritage | John T. Fallon, Jr. |
| 2008 | Mad Jack | Jack Hamilton |
| 2009 | Heritage | John T Fallon,.Jr. |
| 2010 | Aurora | Holly Edmonds |
| 2011 | Smoke | B. Francis Saul, III |
| 2012 | Mad Jack | Jack Hamilton |
| 2013 | Smoke | Joe Lotuff |
| 2014 | Smoke | Joe Lotuff |
| 2015 | Smoke | Joe Lotuff |
| 2016 | Aurora | Holly Edmonds |
| 2017 | Mad Jack | Jack Hamilton |
| 2018 | Madeline | Henry & Eli Burnes |
| 2019 | Mad Jack | Jack Hamilton |
| 2020 | Pandemic – Trophy Not Awarded | |
| 2021 | Smoke | Jack Howard |
| 2022 | Smoke | Clark Lotuff |
| 2023 | Heritage | Anthony Shriver |
| 2024 | Kerplunk | Kent Plunkett |