| Bennet Trophy (Smythe) |
| 1975 | John Skinner (Shrewsbury S&YC) |
| 1976 | Edward Rowe (Shrewsbury S&YC) |
| 1977 | Steve Grove (Little Egg Harbor YC) |
| 1978 | Lieghton Waters (Shrewsbury S&YC) |
| 1979 | Christopher Quigley (Brant Beach YC) |
| 1980 | Thomas Fink (Monmouth BC) |
| 1981 | Michael Mergenthaler (Monmouth BC) |
| 1982 | John Brady (Hunterdon SC) |
| 1983 | Susan Lawser (Monmouth BC) |
| 1984 | Susan Lawser (Monmouth BC) |
| 1985 | Susan Lawser (Monmouth BC) |
| 1986 | Matt Smith (Monmouth BC) |
| 1987 | Roger Marino (Monmouth BC) |
| 1988 | Roger Marino (Monmouth BC) |
| 1989 | Greg Beshore (Shrewsbury S&YC) |
| 1990 | Nathan Marsh (Monmouth BC) |
| 1991 | Stephen Young (Monmouth BC) |
| 1992 | Steve Wright (Spray Beach YC) |
| 1993 | Steve Wright (Spray Beach YC) |
| 1994 | Steve Wright (Spray Beach YC) |
| 1995 | Talbott Ingram (Shrewsbury S&YC) |
| 1996 | Talbott Ingram (Shrewbury S&YC) |
| 1997 | Kelly Gruskos (Shrewsbury S&YC) |
| 1998 | Rob Kunkel (SCYC) |
| 1999 | Roger Kunkel (SCYC) |
| 2000 | Jeff Bonnani (SSYC) |
| 2001 | Frank Demmerly (LEHYC) |
| 2002 | Sam Gilbert (LEHYC) |
| 2003 | Kyle Kovacs (BBYC) |
| 2004 | Theo Ingram (SSYC) |
| 2005 | Greg Hahl (BBYC) |
| 2006 | Jeff Hahl (BBYC) |
| 2007 | Jeff Hahl (BBYC) |
| 2008 | Max Lopez (Monmouth Boat Club) |
| 2009 | Jack Swikart ( SSYC) |
| 2010 | NOT SAILED |