Frederic F. Scudder Memorial Trophy
Class Championship Series, First Overall
| Year | Yacht | Skipper |
| 1949 | No Name (73) | Benjamin Baxter |
| 1950 | No Name (73) | Benjamin Baxter |
| 1951 | Blue Boy III (46) | Gardner Schirmer |
| 1952 | No Name (73) | Benjamin Baxter |
| 1953 | Mimi (36) | W.R. Sinclair |
| 1954 | Bettayet (117) | Ross W. Richards |
| 1955 | Hurricane – Trophy Not Awarded | |
| 1956 | Hermanos (76) | Allan L. Priddy |
| 1957 | Bettayet (117) | Ross W. Richards |
| 1958 | Dungolphin (109) | Durban A. McGraw |
| 1959 | Marna (120) | John T. Fallon |
| 1960 | Marna (120) | John T. Fallon |
| 1961 | Venture (85) | David D. Steere |
| 1962 | Uncle Benny (73) | Stanley W. Moore |
| 1963 | Venture (85) | David D. Steere |
| 1964 | Marna (120) | John T. Fallon |
| 1965 | Marna (120) | John T. Fallon |
| 1966 | Uncle Benny (73) | Stanley W. Moore |
| 1967 | Marna (120) | John T. Fallon |
| 1968 | Marna (120) | John T. Fallon |
| 1969 | Bettawin (141) | Ross W. Richards |
| 1970 | Marna (120) | John T. Fallon |
| 1971 | Cirrus (136) | George P. Edmonds, Jr. |
| 1972 | Venture (85) | David D. Steere |
| 1973 | Cirrus (136) | George P. Edmonds, Jr. |
| 1974 | Marna (120) | John T. Fallon |
| 1975 | Pertelote (143) | Boardman Lloyd |
| 1976 | Marna (120) | John T. Fallon |
| 1977 | Stanley Steamer (163) [173] | Stanley W. Moore |
| 1978 | Invader (169) | Lewis J.H. Gunn |
| 1979 | Invader (169) | Lewis J.H. Gunn |
| 1980 | Invader (169) | Lewis J.H. Gunn |
| 1981 | Lucky Lady (172) | Bradford W. Tracy |
| 1982 | Pertelote (143) | Boardman Lloyd |
| 1983 | Pertelote (143) | Francis V. Lloyd, III |
| 1984 | Cochenoe (125) | Donald F. Law, Jr. |
| 1985 | Cochenoe (125) | Donald F. Law, Jr. |
| 1986 | Cochenoe (125) | Donald F. Law, Jr. |
| 1987 | Cochenoe (125) | Donald F. Law, Jr. |
| 1988 | Scarlet (163) [173] | Thomas H. O’Toole |
| 1989 | Cochenoe (125) | Donald F. Law, Jr. |
| 1990 | Eight Ball (142) | Karl E. Anderson |
| 1991 | Marna (120) | John T. Fallon, Jr. |
| 1992 | Cirrus (136) | Alden Edmonds |
| 1993 | Cochenoe (125) | Donald F. Law, Jr. |
| 1994 | Eight Ball (142) | Karl E. Anderson |
| 1995 | Marna (120) | John T. Fallon, Jr. |
| 1996 | Cochenoe (125) | Andrew Pesek |
| 1997 | Marna (120) | John T. Fallon, Jr. |
| 1998 | Rapparee (177) | Peter L. O’Keeffe |
| 1999 | Scarlet (163) [173] | Burt McManus |
| 2000 | Yankee Dime (145) | Alden Edmonds |
| 2001 | Pieces of 8 (188) | Karl E. Anderson |
| 2002 | Yankee Dime (145) | B. Francis Saul, III |
| 2003 | Pieces of 8 (188) | Karl E. Anderson |
| 2004 | Pieces of 8 (188) | Todd Kittredge |
| 2005 | Aurora (200) | Holly Edmonds |
| 2006 | Pieces of 8 (188) | Todd Kittredge |
| 2007 | Yankee Dime (150) | B. Francis Saul III |
| 2008 | Cochenoe (197) | Donald F. Law, Jr. |
| 2009 | Mad Jack (206) | Jack Hamilton |
| 2010 | Smoke (214) | B. Francis Saul, III |
| 2011 | Pieces of 8 (188) | Heather Gregg |
| 2012 | Smoke (214) | Richard Feeny |
| 2013 | Beltane (222) | Jim Cunningham |
| 2014 | Madeline (207) | Gordon Burnes |
| 2015 | Heritage (199) | John T Fallon, Jr |
| 2016 | Scout (220) | Kelsey Wheeler |
| 2017 | Kerplunk (225) | Kent Plunkett |
| 2018 | Mad Jack (206) | Jack Hamilton |
| 2019 | Madeline (207) | Eli and Henry Burnes |
| 2020 | Pandemic – Trophy Not Awarded | |
| 2021 | Kerplunk (225) | Kent Plunkett |
| 2022 | Kerplunk (225) | Kent Plunkett |
| 2023 | Aria (213) | Peter Shope |
| 2024 | Aria (213) | Peter Shope |
| 2025 | Aria (213) | Peter Shope |
H. Manley Crosby Memorial Trophy
Class Championship Series, Second Overall
| Year | Yacht | Skipper |
| 1960 | Venture (85) | David D. Steere |
| 1961 | Marna (120) | John T. Fallon |
| 1962 | Venture (85) | David D. Steere |
| 1963 | Marna (120) | John T. Fallon |
| 1964 | Venture (85) | David D. Steere |
| 1965 | Venture (85) | David D. Steere |
| 1966 | Victura (94) | Edward M. Kennedy |
| 1967 | Phebe (117) | Robert T. Gill |
| 1968 | Cirrus (136) | George P. Edmonds, Jr. |
| 1969 | Uncle Benny (73) | Stanley W. Moore |
| 1970 | Bettawin (141) | Ross W. Richards |
| 1971 | Pertelote (143) | Malcolm Lloyd |
| 1972 | Marna (120) | John T. Fallon |
| 1973 | Pertelote (143) | Boardman Lloyd |
| 1974 | Pertelote (143) | Francis V. Lloyd, III |
| 1975 | Marna (120) | John T. Fallon |
| 1976 | Victura (194) [167] | Joseph P. Kennedy, II |
| 1977 | Relentless (155) | Jeffrey Hurst |
| 1978 | Sovereign V (145) | Harrison P. Bridge |
| 1979 | Cirrus (136) | George P. Edmonds, Jr. |
| 1980 | Molly (158) | Alan T. McDonough |
| 1981 | Marna (120) | John T. Fallon |
| 1982 | Lucky Lady (172) | Bradford W. Tracy |
| 1983 | Cochenoe (125) | Donald F. Law, Jr. |
| 1984 | Marna (120) | John T. Fallon |
| 1985 | Snow Goose (161) | Lewis J.H. Gunn |
| 1986 | Marna (120) | John T. Fallon |
| 1987 | Scarlet (163) [173] | Thomas H. O’Toole |
| 1988 | Cochenoe (125) | Donald F. Law, Jr. |
| 1989 | Eight Ball (142) | Karl E. Anderson |
| 1990 | Invader (184) | Lewis J.H. Gunn |
| 1991 | Cochenoe (125) | Kevin C. Cain |
| 1992 | Eight Ball (142) | Karl E. Anderson |
| 1993 | Cirrus (136) | Holly Edmonds |
| 1994 | Cochenoe (125) | Sara Molyneaux |
| 1995 | Eight Ball (142) | Karl E. Anderson |
| 1996 | Cirrus (136) | Holly Edmonds |
| 1997 | Eight Ball (142) | Karl E. Anderson |
| 1998 | Invader (184) | Lewis J.H. Gunn |
| 1999 | Eight Ball (142) | Karl E. Anderson |
| 2000 | Scarlet (163) [173] | Burt McManus |
| 2001 | Yankee Dime (145) | Gordon Burnes |
| 2002 | Lente Festina (184) | G. Kent Plunkett |
| 2003 | Lente Festina (184) | G. Kent Plunkett |
| 2004 | Eowyn (202) | George Largay |
| 2005 | Dauntless (195) | Jeffrey Tracy |
| 2006 | Heritage (199) | John T. Fallon, Jr. |
| 2007 | Mad Jack (206) | Jack Hamilton |
| 2008 | Heritage (199) | John T. Fallon, Jr. |
| 2009 | Eowyn (202) | George Largay |
| 2010 | Pieces of 8 (188) | Heather Gregg |
| 2011 | Eowyn (202) | Tim Wadlow |
| 2012 | Beltane (222) | Jim Cunningham |
| 2013 | Madeline (207) | Gordon Burnes |
| 2014 | Heritage (199) | John T Fallon, Jr. |
| 2015 | Mad Jack (206) | Jack Hamilton |
| 2016 | Mad Jack (206) | Jack Hamilton |
| 2017 | Scout (220) | Sophie Pesek |
| 2018 | Kerplunk (225) | Kent Plunkett |
| 2019 | Kerplunk (225) | Kent Plunkett |
| 2020 | Pandemic – Trophy Not Awarded | |
| 2021 | Mad Jack (206) | Jack Hamilton |
| 2022 | Scout (220) | Fraser Pesek |
| 2023 | Scout (220) | Fraser Pesek |
| 2024 | Scout (220) | Fraser Pesek |
| 2025 | Smoke (214) | Joe Lotuff |
Ross W. Richards Memorial Trophy
Class Championship Series, Third Overall
| Year | Yacht | Skipper |
| 1973 | Invader (134) | Lewis J.H. Gunn |
| 1974 | Cirrus (136) | George P. Edmonds, Jr. |
| 1975 | No Name (153) | Arthur R. Greene, Jr. |
| 1976 | We’re Here (129) | Connie M. Tracy |
| 1977 | Cirrus (136) | George P. Edmonds, III |
| 1978 | Relentless (155) | Jeffrey Hurst |
| 1979 | Pertelote (143) | Boardman Lloyd |
| 1980 | Madeline (148) | Richard M. Burnes, Jr. |
| 1981 | Invader (169) | Lewis J.H. Gunn |
| 1982 | Marna (120) | John T. Fallon |
| 1983 | Cirrus (136) | George P. Edmonds, Jr. |
| 1984 | Steamer (163) [173] | Thomas H. O’Toole |
| 1985 | Pertelote (143) | Malcolm Lloyd |
| 1986 | Molly (158) | Alan T. McDonough |
| 1987 | Invader (174) | Lewis J.H. Gunn |
| 1988 | Molly (158) | Alan T. McDonough |
| 1989 | Marna (120) | John T. Fallon, Jr. |
| 1990 | Scarlet (163) [173] | Thomas H. O’Toole |
| 1991 | Eight Ball (142) | Karl E. Anderson |
| 1992 | Cochenoe (125) | Andrew Pesek |
| 1993 | Althea (185) | Richard M. Burnes, Jr. |
| 1994 | Molly (158) | John T. McDonough |
| 1995 | Cochenoe (125) | Kevin C. Cain |
| 1996 | Eight Ball (142) | Ian McNiece |
| 1997 | Sea Lyon (174) | Charles M. Lyons |
| 1998 | Scarlet (163) [173] | Jean O. McManus |
| 1999 | Lente Festina (184) | G. Kent Plunkett |
| 2000 | Cirrus (136) | Holly Edmonds |
| 2001 | Lente Festina (184) | G. Kent Plunkett |
| 2002 | Pieces of 8 (188) | Karl Anderson |
| 2003 | Rapparee (177) | Peter L. O’Keeffe |
| 2004 | Aurora (200) | Holly Edmonds |
| 2005 | Pieces of Eight (188) | Todd Kittredge |
| 2006 | Dauntless (195) | Jeffrey Tracy |
| 2007 | Heritage (199) | John T. Fallon, Jr. |
| 2008 | Mad Jack (206) | Jack Hamilton |
| 2009 | Heritage (199) | John T Fallon,.Jr. |
| 2010 | Aurora (200) | Holly Edmonds |
| 2011 | Smoke (214) | B. Francis Saul, III |
| 2012 | Mad Jack (206) | Jack Hamilton |
| 2013 | Smoke (214) | Joe Lotuff |
| 2014 | Smoke (214) | Joe Lotuff |
| 2015 | Smoke (214) | Joe Lotuff |
| 2016 | Aurora (200) | Holly Edmonds |
| 2017 | Mad Jack (206) | Jack Hamilton |
| 2018 | Madeline (207) | Henry & Eli Burnes |
| 2019 | Mad Jack (206) | Jack Hamilton |
| 2020 | Pandemic – Trophy Not Awarded | |
| 2021 | Smoke (214) | Jack Howard |
| 2022 | Smoke (214) | Clark Lotuff |
| 2023 | Heritage (199) | Anthony Shriver |
| 2024 | Kerplunk (225) | Kent Plunkett |
| 2025 | Kerplunk (225) | Kent Plunkett |