Presented in 1949 by the Commodores of the Club who held office from its organization in 1938 to 1949, the award was presented to the skipper of the winning yacht under 20 feet LWL in the FBYC annual long-distance race. In 1976, the Board expanded the group under consideration for the Commodores Bowl designating the award be presented to the outstanding Skipper in Fishing Bay Yacht Club sponsored sailing events for the year, based upon performance and participation. The award was presented on a alternating year basis to the Offshore and One Design Skipper.
In 2023, the Trustees wishing to continue to recognize FBYC members’ outstanding achievements in the world of sailing expanded consideration of the award to include skippers in all divisions across the full range of sailing endeavors.
The Commodores Bowl shall be awarded to the skipper, who is a member of Fishing Bay Yacht Club, for their outstanding achievements in the world of sailing which includes racing, endurance events and accomplishments in voyaging. Selection for this award should consider the quality of events, the rarity of the achievement, and performance in FBYC and non-FBYC events. The selection of the recipient of this trophy shall be determined by the Commodore. The Commodore may appoint a committee to determine the winner of the trophy.
| 1949 | Reid A. Dunn | |
| 1950 | J. Marshall Moseley | |
| 1951 | Constance Hicks | |
| 1952 | Lloyd N. Emory | |
| 1953 | J. Marshall Moseley | |
| 1954 | Constance Hicks | |
| 1955 | Constance Hicks | |
| 1956 | Anne & Margaret Eppes | |
| 1957 | George C. Roper, Jr. | |
| 1958 | Anne Eppes | |
| 1959 | Anne Eppes | |
| 1960 | Roger Moorman | |
| 1961 | Andrew Sinnickson | |
| 1962 | Roger Moorman | |
| 1963 | Andrew Sinnickson | |
| 1964 | Frank D. Hargrove | |
| 1965 | Raymond J. Munsch | |
| 1966 | G. R. and B. D. Prout | |
| 1967 | Charles Modjeski | |
| 1968 | John Hawksworth | |
| 1969 | B. Matthew Hulcher | |
| 1970 | Raymond J. Munsch | |
| 1971 | Peter Roughton | |
| 1972 | Chuck Raynor | |
| 1973 | Stuart Tyson | |
| 1974 | Fred L. Williams, Jr. | |
| 1975 | Matt Bounds | |
| 1976 | Raymond J. Munsch | |
| 1977 | Charles S. Squires | |
| 1978 | Matthew Bounds | |
| 1979 | Brent Halsey & Mayo Tabb | |
| 1980 | F. Case Whittemore | |
| 1981 | John R. Hawksworth | |
| 1982 | James T. Poindexter, III | |
| 1983 | H. Seward Lawlor | |
| 1984 | Bob W. Walker | |
| 1985 | Harrison Hubard, Jr. | |
| 1986 | F. Case Whittemore | |
| 1987 | Thomas E. Whittle | |
| 1988 | Alain Vincey | |
| 1989 | James F. Lipscomb, Jr. | |
| 1990 | Gene Roberts | |
| 1991 | Brenton S. Halsey | |
| 1992 | H. Bradshaw Squires | |
| 1993 | Kathleen S. Whittle | |
| 1994 | William F. Bowie | |
| 1995 | Paul Andersen | |
| 1996 | H. Bradshaw Squires | |
| 1997 | James E. Rogers | |
| 1998 | H. Bradshaw Squires | |
| 1999 | Robert M. Whittet | |
| 2000 | John C. Beery | |
| 2001 | Michael W. Karn | |
| 2002 | Philip H. Webb | |
| 2003 | Eric R. Powers | |
| 2004 | Lee M. Farinholt | |
| 2005 | D. Bradford Miller | |
| 2006 | Jonathan M. Deutsch | |
| 2007 | J. Bradley Davis | |
| 2008 | Michael B. Miller | |
| 2009 | Wayland W. Rennie | |
| 2010 | Mathew J. Braun | |
| 2011 | D. Bradford Miller | |
| 2012 | John B. Wake, Jr. | |
| 2013 | Robert J. & Lisa Fleck | |
| 2014 | Len Guenther | |
| 2015 | Robert J. & Lisa Fleck | |
| 2016 | Charles Brewer | |
| 2017 | Craig Wright | |
| 2018 | John Wake | |
| 2019 | Bob Fleck | |
| 2020 | John Wake | |
| 2021 | David Clark | |
| 2022 | Philip H. Webb | |
| 2023 | David Tabor |