Bass River Yacht Club Regatta
Bass River Challenge Cup
| Year | Yacht | Skipper |
| 1956 | Alert | Richard P. O’Leary |
| 1957 | Bettayet | Ross W. Richards |
| 1958 | Hermanos | Allan L. Priddy |
| 1959 | High Barbaree | Barbara Barre |
| 1960 | Mimi | Dora S. Loutrel |
| 1961 | Venture | David D. Steere |
| 1962 | Uncle Benny | Stanley M. Moore |
| 1963 | Sovereign IV | Harrison P. Bridge |
| 1964 | Marna | John T. Fallon |
| 1965 | Marna | John T. Fallon |
| 1966 | Phebe | Robert Gill |
| 1967 | Phebe | Robert Gill |
| 1968 | Marna | John T. Fallon |
| 1969 | Bettawin | Ross W. Richards |
| 1970 | Uncle Benny | Stanley W. Moore |
| 1971 | Invader | Lewis J.H. Gunn |
| 1972 | Shamrock | Francis C. O’Neil, Jr. |
| 1973 | Kim II | William S. Kimball |
| 1974 | Pertelote | Francis V. Lloyd, III |
| 1975 | Pertelote | Boardman Lloyd |
| 1976 | Invader | Lewis J.H. Gunn |
| 1977 | Venture | David D. Steere |
| 1978 | No Race | |
| 1979 | Venture | David D. Steere |
| 1980 | Stanley Steamer | Stanley W. Moore |
| 1981 | Lucky Lady | Bradford W. Tracy |
| 1982 | Marna | John T. Fallon, Jr. |
| 1983 | Cheetah | Eric K. Bacon |
| 1984 | Steamer | Thomas H. O’Toole |
| 1985 | Marna | William J. Fallon |
| 1986 | Cochenoe | Donald F. Law, Jr. |
| 1987 | Escapade | Barry W. Plunkett, Jr. |
| 1988 | Cirrus | Holly Edmonds |
| 1989** | Eight Ball | Karl E. Anderson |
| 1990 | Scarlet | Thomas H. O’Toole |
| 1991 | Cochenoe | Kevin C. Cain |
| 1992 | Eight Ball | Karl E. Anderson |
| 1993 | Cirrus | Holly Edmonds |
| 1994 | Molly | John T. McDonough |
| 1995 | Althaea | Nonnie Burnes |
| 1996 | Victura | Edward M. Kennedy, Jr. |
| 1997 | Marna | John T. Fallon, Jr. |
| 1998 | Rapparee | Peter L. O’Keeffe |
| 1999 | Eight Ball | Karl E. Anderson |
| 2000 | Yankee Dime | Alden Edmonds |
| 2001 | Pieces of 8 | Karl E. Anderson |
| 2002 | Lente Festina | G. Kent Plunkett |
| 2003 | No Race – High Winds | |
| 2004 | Aurora | Holly Edmonds |
| 2005 | Cheerful | Lloyd McManus, Jr. |
| 2006 | Dauntless | Jeffrey Tracy |
| 2007 | Aurora | Holly Edmonds |
| 2008 | Heritage | John T. Fallon, Jr. |
| 2009 | Yankee Dime | Ben Sullivan |
| 2010 | Pieces of 8 | Heather Gregg |
| 2011 | Eowyn | Tim Wadlow |
| 2012 | Smoke | Richard Feeny |
| 2013 | Aurora | Holly Edmonds |
| 2014*** | Madeline | Gordon Burnes |
| 2015 | Scout | Sophie Pesek |
| 2016 | Mad Jack | Jack Hamilton |
| 2017 | Scout | Sophie Pesek |
| 2018 | Smoke | Joe Lotuff |
| 2019 | Kerplunk | Kent Plunkett |
| 2020 | Aria | Mary Fulham |
| 2021 | No Race – High Winds | |
| 2022 | Scout | Fraser Pesek |
| 2023 | Madeline | Eli Burnes |
| 2024 | Three Sticks | Peter MvAvoy |
| 2025 | Smoke | Joe Lotuff |
** 75th Anniversary Weekend
*** 100th Anniversary Weekend