Circuit Overall – Spinnaker
2024 Winner – Checkered Demon – Holland T/2 – Neal & OJ O’Connell
| Year | Boat | Type | Skipper |
| 1970 | SUE-SUE | MORGAN 24 | T. M. Russell III |
| 1971 | ALETHEA | C&C35 | J. & M. HOLSTEIN |
| 1972 | HABONDIA | RANGER 26 | W. & P. CANNING |
| 1973 | HABONDIA | RANGER 26 | W. & P. CANNING |
| 1974 | POITIN | EVELYN 24 | BOB EVELYN |
| 1975 | TOAD HALL | CANNING 24 | W. & P. CANNING |
| 1976 | RAGTIME | J24 | R. JOHNSTONE |
| 1977 | FORMULA I | EVELYN 36 | R. EVELYN & B. HALL |
| 1978 | SUGAH | CAL29 | R. ABERCROMBIE |
| 1979 | ANNELIESE | VENTURE 24 | J. HALE |
| 1980 | ANNELIESE | VENTURE 24 | J. HALE |
| 1981 | JAZZ | J36 | R. JOHNSTONE |
| 1982 | ANNELIESE | VENTURE 24 | J. HALE |
| 1983 | NEW WAVE | EVELYN 26 | PAUL HEWITT |
| 1984 | RAGTIME | J24 | R. JOHNSTONE |
| 1985 | STAINLESS | EVELYN 42 | R. EVELYN/BURGESS |
| 1986 | ANNELIESE | EVELYN 32 | J.HALE |
| 1987 | ALGERNON | COL 26 | C SEELGEN |
| 1988 | ANNELIESE | EVELYN 32 | J.HALE |
| 1989 | TOUCH OF GRAY | J35 | GOWRIE/GOSS/CONNOLLY |
| 1990 | TOAD HALL | EVELYN 25 | W. CANNING |
| 1991 | TOUCH OF GRAY | J35 | GOWRIE/GOSS/CONNOLLY |
| 1992 | STRANGE | PEARSON 30 | R. STERNICKI |
| 1993 | WILDTHING | EVELYN 32 | K. FARRAR |
| 1994 | LADY JANE | J27 | E. BECKER |
| 1995 | PROPHET | EVELYN 26 | DON WILKINSON |
| 1996 | HAWK | J29 | PAUL CONNOR |
| 1997 | HOT NUMBERS | TAYLOR 42 | CONNOLLY/KARENKO |
| 1998 | JOYRIDE | EVELYN 32 | BUSTER KINGSBURY, JR. |
| 1999 | SECRET | NELSON MAREK 42 | BRUCE KURYLA |
| 2000 | CHECKERED DEMON | HOLLAND | NEAL O’CONNELL |
| 2001 | SECRET | NELSON MAREK 42 | BRUCE KURYLA |
| 2002 | SECRET | NELSON MAREK 42 | BRUCE KURYLA |
| 2003 | SECRET | NELSON MAREK 42 | BRUCE KURYLA |
| 2004 | DR. EVIL | OLSON 29 | TOM TREAT |
| 2005 | EN CHARETTE | NOE 27 | PAUL JENNINGS |
| 2006 | SECRET | NELSON MAREK 42 | BRUCE KURYLA |
| 2007 | EN CHARETTE | NOE 27 | PAUL JENNINGS |
| 2008 | WOLVERINE | FRERS 33 | DAVID NAUBER |
| 2009 | SECRET | NELSON MAREK 42 | BRUCE KURYLA |
| 2010 | SECRET | NELSON MAREK 42 | BRUCE KURYLA |
| 2011 | WOLVERINE | FRERS 33 | DAVID NAUBER |
| 2012 | SECRET | NELSON MAREK 42 | BRUCE KURYLA |
| 2013 | SECRET | NELSON MAREK 42 | BRUCE KURYLA |
| 2014 | TIE BETWEEN SECRET / WOVLERINE |
NELSON MAREK 42FRERS 33 | BRUCE KURYLADAVID NAUBER |
| 2015 | SECRET | NELSON MAREK 42 | BRUCE KURYLA |
| 2016 | PACHYDERM | FRERS 33 | EDGAR SMITH |
| 2017 | MILFORD SAILING FOUNDATION | MELGES 32 | BRUCE KURYLA |
| 2018 | SNOW BIRD | SCHOCK 35 | PAUL VON MAFFEI |
| 2019 | DETAILS | ANDREWS 30 Mk1 | JOHN FRIES |
| 2020 | MILFORD SAILING FOUNDATION | MELGES 32 | BRUCE KURYLA |
| 2021 | WOLVERINE | FRERS 33 | DAVID NAUBER |
| 2022 | MILFORD SAILING FOUNDATION | MELGES 32 | BRUCE KURYLA |
| 2023 | MILFORD SAILING FOUNDATION | MELGES 32 | BRUCE KURYLA |
| 2024 | CHECKERED DEMON | HOLLAND T/2 | NEAL & OJ O’Connell |