The Sailor of the Year Award is decided by the Commodore and presented at the Commodore's Ball.
  • 2010 Jack Davies
  • 2009 Cam Lewis
  • 2008 Jeff Pulford
  • 2007 Robin Jeffers
  • 2006 Tracy Usher
  • 2005 Tracy Usher
  • 2004 Tracy Usher
  • 2003 Donna Womble
  • 2002 Jeff Pulford & Larry Gamble
  • 2001 Patrick Whitmarsh & Paul Allen
  • 2000 Karen Loutzenheiser
  • 1999 Mark Chandler & Richard M. Clark
  • 1998 (not awarded)
  • 1997 Bill Keller
  • 1996 Bill Keller & Mike Martin
  • 1995 Brent Harrill & Brenden Richards
  • 1994 David Morris
  • 1993 Blake Quinn
  • 1992 George Penley
  • 1991 Patrick Bradley
  • 1990 Charles Jacobson
  • 1989 Charles Jacobson
  • 1988 Marty Nation and Steven Rasmussen
  • 1987 Charles Jacobson
  • 1986 Richard M. Clark
  • 1985 Richard M. Clark
  • 1984 Michael Polkabla
  • 1983 Mark Chandler
  • 1982 Michael Polkabla
  • 1981 (not awarded)
  • 1980 Patrick Bradley
  • 1979 Jack McAleer
  • 1978 Richard M. Clark
  • 1977 (not awarded)
  • 1976 Cole Weston
  • 1975 Richard M. Clark
  • 1974 (not awarded)
  • 1973 Harvey V. Kilpatrick
  • 1972 Chris Gould