2007 - no award
2006 - J.D. Reddaway (Suwanee, GA)
2005 - Midshipman Greg Storer (Annapolis, MD/Branford, CT)
2004 - Frederick "Bo" Smith (Birmingham, Ala.)
2003 - Olin J. Stephens (Hanover, NH) Honor Roll
2002 - Henry Maxwell, Jr. (Stonington, CT) Honor Roll
2001/02 - George Fisher (Columbus, OH) Honor Roll
2000/01 - Dave Perry (Southport, CT) Honor Roll
1999/00 - William B. Ross (Mooresville, NC)
1998/99 - Joey Harris (Chicago, IL)
1997/98 - Gonzalo Diaz Sr. (Miami, FL)
1996/97 - Richard W. Besse (Skaneateles, NY)
1995/96 - Harry Carpenter (Oakland, MD)
1994/95 - Jessica Uniack (Huntington Beach, CA)
1993/94 - Newport Harbor High School Sailing Team (Newport Beach, CA)
1992/93 - George Antarr (Marina del Rey, CA)
1991/92 - Dick Ronan (Larchmont, NY)
1990/91 - Scott Steele (Annapolis, MD)
1989/90 - John Odenbach, Sr. (Penfield, NY)
1988/89 - Runyon Colie (Mantoloking, NJ)
1987/88 - Hub Isaacks (Ft. Worth, TX)
1986/87 - Buddy Melges (Zenda, WI)