Bass River Yacht Club Regatta
Bass River Challenge Cup
| Year | Yacht | Skipper |
| 1956 | Alert (87) | Richard P. O’Leary |
| 1957 | Bettayet (117) | Ross W. Richards |
| 1958 | Hermanos (76) | Allan L. Priddy |
| 1959 | High Barbaree (119) | Barbara Barre |
| 1960 | Mimi (36) | Dora S. Loutrel |
| 1961 | Venture (85) | David D. Steere |
| 1962 | Uncle Benny (73) | Stanley M. Moore |
| 1963 | Sovereign IV (83) | Harrison P. Bridge |
| 1964 | Marna (120) | John T. Fallon |
| 1965 | Marna (120) | John T. Fallon |
| 1966 | Phebe (117) | Robert Gill |
| 1967 | Phebe (117) | Robert Gill |
| 1968 | Marna (120) | John T. Fallon |
| 1969 | Bettawin (141) | Ross W. Richards |
| 1970 | Uncle Benny (73) | Stanley W. Moore |
| 1971 | Invader (134) | Lewis J.H. Gunn |
| 1972 | Shamrock (144) | Francis C. O’Neil, Jr. |
| 1973 | Kim II (118) | William S. Kimball |
| 1974 | Pertelote (143) | Francis V. Lloyd, III |
| 1975 | Pertelote (143) | Boardman Lloyd |
| 1976 | Invader (169) | Lewis J.H. Gunn |
| 1977 | Venture (85) | David D. Steere |
| 1978 | No Race | |
| 1979 | Venture (85) | David D. Steere |
| 1980 | Stanley Steamer (163) [173] | Stanley W. Moore |
| 1981 | Lucky Lady (172) | Bradford W. Tracy |
| 1982 | Marna (120) | John T. Fallon, Jr. |
| 1983 | Cheetah (166) | Eric K. Bacon |
| 1984 | Steamer (163) [173] | Thomas H. O’Toole |
| 1985 | Marna (120) | William J. Fallon |
| 1986 | Cochenoe (125) | Donald F. Law, Jr. |
| 1987 | Escapade (112) | Barry W. Plunkett, Jr. |
| 1988 | Cirrus (136) | Holly Edmonds |
| 1989** | Eight Ball (142) | Karl E. Anderson |
| 1990 | Scarlet (163) [173] | Thomas H. O’Toole |
| 1991 | Cochenoe (125) | Kevin C. Cain |
| 1992 | Eight Ball (142) | Karl E. Anderson |
| 1993 | Cirrus (136) | Holly Edmonds |
| 1994 | Molly (158) | John T. McDonough |
| 1995 | Althaea (185) | Nonnie Burnes |
| 1996 | Victura (167) [194] | Edward M. Kennedy, Jr. |
| 1997 | Marna (120) | John T. Fallon, Jr. |
| 1998 | Rapparee (177) | Peter L. O’Keeffe |
| 1999 | Eight Ball (142) | Karl E. Anderson |
| 2000 | Yankee Dime (145) | Alden Edmonds |
| 2001 | Pieces of 8 (188) | Karl E. Anderson |
| 2002 | Lente Festina (184) | G. Kent Plunkett |
| 2003 | No Race – High Winds | |
| 2004 | Aurora (200) | Holly Edmonds |
| 2005 | Cheerful (142) | Lloyd McManus, Jr. |
| 2006 | Dauntless (195) | Jeffrey Tracy |
| 2007 | Aurora (200) | Holly Edmonds |
| 2008 | Heritage (199) | John T. Fallon, Jr. |
| 2009 | Yankee Dime (150) | Ben Sullivan |
| 2010 | Pieces of 8 (188) | Heather Gregg |
| 2011 | Eowyn (202) | Tim Wadlow |
| 2012 | Smoke (214) | Richard Feeny |
| 2013 | Aurora (200) | Holly Edmonds |
| 2014*** | Madeline (207) | Gordon Burnes |
| 2015 | Scout (220) | Sophie Pesek |
| 2016 | Mad Jack (206) | Jack Hamilton |
| 2017 | Scout (220) | Sophie Pesek |
| 2018 | Smoke (214) | Joe Lotuff |
| 2019 | Kerplunk (225) | Kent Plunkett |
| 2020 | Aria (213) | Mary Fulham |
| 2021 | No Race – High Winds | |
| 2022 | Scout (220) | Fraser Pesek |
| 2023 | Madeline (207) | Eli Burnes |
| 2024 | Three Sticks (212) | Peter McAvoy |
| 2025 | Smoke (214) | Joe Lotuff |
** 75th Anniversary Weekend
*** 100th Anniversary Weekend