Fleet Championship History
| Year | Boat Number | Boat Name | 1st Place Skipper | 1st Place Crew | 2nd Place | 3rd Place |
|---|
| 2007 | 8245 | Brillo | Joe Zambella | Greg Dolan | Hornos | Braverman |
| 2006 | 7793 | Pampero | Tomas Hornos | Luis Hornos | Costa | Woods |
| 2005 | 7629 | | Ken Woods | Howard Davis | MacDonald | Sandstrom |
| 2004 | 8052 | Don't Look Back | Stephen Braverman | Cindy Olsen | Woods | Rosen |
| 2003 - tie | 8052 | Don't Look Back | Stephen Braverman | Ron Rezac | | |
| 2003 - tie | 7732 | Night Light | Gary MacDonald | Howard Davis | | |
| 2002 | 7732 | Night Light | Gary MacDonald | Howard Davis | Braverman | Charles |
| 2001 | 7732 | Night Light | Gary MacDonald | Howard Davis | Braverman | Woods |
| 2000 | 7629 | | Ken Woods | Bill Paton | Braverman | Zambella |
|
| 1999 | 7621 | Owl | Peter Costa | Jessica Costa | Braverman | Charles |
| 1998 | 7628 | | Stephen Braverman | Ron Rezac | Larson | Costa |
| 1997 | 7828 | | Jack Slattery | Doug Brophy | Vessella | Charles |
| 1996 | 7728 | Stars & Snipes | Ron Sandstrom | Kurt Larson | Gast | Woods |
| 1995 | 7072 | Night Light | Gary MacDonald | Greg Bernstein | Sandstrom | Cavicchi |
| 1994 | | Stars & Snipes | Ron Sandstrom | Bill Paton | | |
| 1993 | | Stars & Snipes | Ron Sandstrom | Bill Paton | | |
| 1992 | | Stars & Snipes | Ron Sandstrom | Mike Marcel | | |
| 1991 | 7468 | Stars & Snipes | Ron Sandstrom | Jeff Bresnehan | | |
| 1990 | 7468 | Stars & Snipes | Ron Sandstrom | Jeff Bresnehan | | |
|
| 1989 | 6572 | Stars & Snipes | Ron Sandstrom | Jeff Bresnehan | | |
| 1988 | 6933 | Brillo | Joe Zambella | Leo Dawson | | |
| 1987 | 7119 | | Steve Ulian | Brian Murphy | | |
| 1986 | 6572 | Owl | Peter Costa | Dave O'Brien | | |
| 1985 | | Not Sailed | | | | |
| 1984 | | Not Sailed | | | | |
| 1983 | 6532 | Brillo | Joe Zambella | Leo Dawson | | |
| 1982 | 6532 | Brillo | Joe Zambella | Leo Dawson | | |
| 1981 | 6530 | Owl | Peter Costa | Dave O'Brien | | |
| 1980 | 6532 | Brillo | Joe Zambella | Leo Dawson | | |
|
| 1979 | 6530 | Owl | Peter Costa | Grace Costa | | |
| 1978 | 6233 | Star of the Sea | Joe Duplin | Ron Sandstrom | | |
| 1977 | | Brillo | Joe Zambella | Leo Dawson | | |
| 1976 | | Star of the Sea | Joe Duplin | Francis X Dolan | | |
| 1975 | | Star of the Sea | Joe Duplin | Francis X Dolan | | |
| 1971 | | Night Light | Gary MacDonald | Cliff MacDonald | | |
| 1970 | | Color Me Gone | Steve Winkler | Dave Winkler | | |
|
| 1969 | | Hoya | Daniel C Mullane | Robert A Webster | | |
| 1968 | | Star of the Sea X | Joseph Duplin | Francis X Dolan | | |
| 1967 | | Banshee | Francis P Mulkerrin | Joseph Ford | | |
| 1966 | | Banshee | Francis P Mulkerrin | Joseph Ford | | |
| 1965 | | Star of the Sea VI | Joseph Duplin | | | |
| 1964 | | Star of the Sea VI | Joseph Duplin | Francis X Dolan | | |
| 1963 | | Star of the Sea IV | Joseph Duplin | Francis X Dolan | | |
| 1962 | | Scalded Cat | Francis X Dolan | Francis P Mulkerrin | | |
| 1961 | | Scalded Cat | Francis X Dolan | Robert Mitchell | | |
| 1960 | | Shamrock | Joseph Duplin | Francis X Dolan | | |
|
| 1959 | | Star Of The Sea II | Joseph Duplin | Richard Gaynor | | |
| 1958 | | Lively Mary | Robert Kirkland | William Parker | | |
| 1957 | | Temptation | Alan McKay | Janet Burke | | |
| 1956 | | Star Of The Sea | Joseph Duplin | James Fitzgerald | | |
| 1955 | | Lively Mary | Robert Kirkland | Thomas Murray | | |
| 1954 | | Delight | Robert Kirkland | Thomas Murray | | |
| 1953 | | Blue Angel | Paul Bishop | Richard Danielson | | |
| 1952 | | Delight | Robert Kirkland | Richard Stard | | |
| 1951 | | Delight | Robert Kirkland | Stuart Nelson | | |
| 1950 | | Renegade | Francis Avakian | Jack Lambert | | |
|
| 1949 | | Renegade | Francis Avakian | Jack Lambert | | |
| 1948 | | Renegade | Francis Avakian | Jack Lambert | | |
| 1947 | | Renegade | Francis Avakian | Jack Lambert | | |
| 1946 | | Nala II | Alan Donkin | Edythe Bright | | |
| 1941 | | Nala II | Alan Donkin | Francis Avakian | | |
| 1940 | | Nala II | Alan Donkin | Francis Avakian | | |
Boston Harbor Star Fleet
