Commodore Gilbert Sheldon Trophy
Commodore Gilbert Sheldon Trophy. Awarded annually to the winner of the Fall Race for Spinnaker Class B. This trophy was donated to the 2000 Club by Gilbert Sheldon. Mr. Sheldon was a friend of First Commodore “Ty” Cobb.
| 1956 | Tango | Ernest H. McVay |
| 1957 | Pavanne | R. Read Shaw |
| 1958 | Tango | Ernest H. McVay |
| 1959 | Mabuhay | Breckenridge Marshall |
| 1960 | Marango | Adelbert A. Goff |
| 1961 | Bean Blossom | Alan V. Young |
| 1962 | Blue Charm | Wallace Sunderland |
| 1963 | Curlew | Frederick W. Thomas |
| 1964 | Precarious | Everett Pearson |
| 1965 | Shady Lady | G. Richard Westin |
| 1966 | Robyn | Frank A. Medeiros |
| 1967 | Mahi Mahi | William H. Shaw |
| 1968 | Lisa Ann | Clinton J. Pearson |
| 1969 | Ragg Doll | John J. Breen. Jr. |
| 1970 | Movourneen | Charles D. Morris |
| 1971 | Nepenthe | Robert W. Read |
| 1972 | No Fall Race | |
| 1973 | Galatea | Robert L. Bowen |
| 1974 | Robyn | Frank A. Medeiros |
| 1975 | No Finishers | |
| 1976 | Volta | Alfred Van Liew |
| 1977 | Jade | Harry Sleicher |
| 1978 | Rondina | Tom Simmonds |
| 1979 | Edelweiss | Aaron Shatkin |
| 1980 | Ain’t Misbehavin’ | John Anderson |
| 1981 | Elan | Barry Carroll |
| 1982 | Admiral “T” | Ron Therrian |
| 1983 | Mischief | Bruce Ferguson |
| 1984 | Right Stuff | Peter Allstrom |
| 1985 | Smiles | Richard A. Carleton |
| 1986-88 | Mischief | Bruce Ferguson |
| 1989 | No Award Presented | |
| 1990 | Nepenthe | Robert W. Read |
| 1991 | Orion | Bob Norton |
| 1992 | Rigadoon | William J. Riggs, Jr. |
| 1993 | Dark Star | Jeff Gibbs |
| 1994 | ‘R Buoy | John Brady |
| 1995 | Dirty Harry | John Lavin |
| 1996 | Mariah | Steven K. Thurston |
| 1997 | Mariah | Steven K. Thurston |
| 1998 | Mariah | Steven K. Thurston |
| 1999 | Morning Dance | Robert Johnston |
| 2000 | Rabbit | Daniel Dyer |
| 2001 | R’Buoy | John & Peg Brady |
| 2002 | Rabbit | Daniel & Mimi Dyer |
| 2003 | Fireball | Don Kern |
| 2004 | Shadow Fox | Steve McCrory |
| 2005 | Falcon | Charles Stoddard |
| 2006 | Party of 4 | Christopher Pearson |
| 2007 | Falcon | Charlie Stoddard |
| 2008 | Thunder | Charley Kineke |
| 2009 | Dark Star | Mark Gervais |
| 2010 | Anser | Peter Allstrom |
| 2011 | Resilience | Curt Spalding |
| 2012 | Falcon | Charlie Stoddard |
| 2013 | Nemesis | Mark Rotsky |
| 2014 | Two Dogs | Moose McClintock |
| 2015 | Vixen | Jim DelBonis |
| 2016 | Flyer | Abbie Seward |
| 2017 | Two Dogs | Moose McClintock |
| 2018 | Two Dogs | Moose McClintock |
| 2019 | Anser | Peter Allstrom |
| 2020 | Mischief | David Schwartz |
