The Benson Cup
Winning Boat & Skipper
| 1981 Gary Boothman |
| 1982 Steve Swanberg |
| 1983 Jim Cardinell |
PERSERVERANCE |
| 1984 Wally Gudgell |
CHAOS |
| 1985 Sunny Vynne |
ALCOR |
| 1986 DNF |
| 1987 Ross Nason |
PENOBSCOT |
| 1988 Wally Gudgell |
RRR |
| 1989 Wes George |
G' DAY |
| 1990 Gary Boothman |
GRASSHOPPER |
| 1991 DNF |
| 1992 DNF |
| 1993 DNF |
| 1994 Bill Glass |
XANADU |
| 1995 George Hiss |
SHARK |
| 1996 DNF |
| 1997 Bill Glass |
BRAVO |
| 1998 Chris White |
PARTHIAN SHOT |
| 1999 George Hiss |
WILD TURKEY |
| 2000 Charles Mottl |
GINNY |
| 2001 Charles Mottl |
GINNY |
| 2002 DNF |
| 2003 Charles Mottl |
GINNY |
| 2004 Bob Brunius |
TIME BANDIT |
| 2005 Michael Kalahar |
MYRRH |
| 2006 Chris White |
NEMESIS |
| 2007 Betsy Wareham |
RED EYE EXPRESS |
| 2008 Bob Brunius |
TIME BANDIT |
| 2009 Chris White |
CRAZY IVAN |
| 2010 Stan & Kay Miller |
STARFIRE |
| 2011 Chris White |
CRAZY IVAN |
| 2012 Jimmy Roser |
CHINOOK |
| 2013 Bob Brunius |
TIME BANDIT |
| 2014 Jimmy Roser |
CHINOOK |
| 2015 Jimmy Roser |
CHINOOK |
| 2016 Bob Brunius |
TIME BANDIT |
| 2017 Betsy Wareham |
PURPLE MARTIN |