Hillcrest Perpetual Trophy

The Hillcrest Perpetual Trophy, a silver cocktail shaker, is awarded to the Class A boat with the best score in the combined races on a Series A race day. Between 1959 and 1996, it was a Class M trophy, donated to that fleet by John Galley to be sailed for annually as close to June 22 as possible. The Hillcrest Perpetual Trophy was rededicated as a Class A trophy in 2007.

• 1959 W. S. Reier
• 1960 Terry Leahy
• 1961 Ed and Jim Smith
• 1962 W. S. Reier
• 1963 Jane Pegel
• 1964 Ed and Jim Smith
• 1965 Jane Pegel
• 1966 Laurie Gray
• 1967 Jane Pegel
• 1968 Jane Pegel
• 1969 Jane Pegel
• 1970 Syd Beers
• 1971 Andy Carlson
• 1972 Jane Pegel
• 1973 Susan Pegel
• 1974 No race
• 1975 Jane Pegel
• 1976 Jane Pegel
• 1977 Susan Pegel
• 1978 Jane Pegel
• 1979 Susan Pegel
• 1980 Harry Melges III
• 1981 Jane Pegel
• 1982 Jane Pegel
• 1983 Jane Pegel
• 1984 Jane Pegel
• 1985 Jane Pegel
• 1986 Jane Pegel
• 1987 No race
• 1988 Jane Pegel
• 1989 Jane Pegel
• 1990 Jane Pegel
• 1991 Jane Pegel
• 1992 Ron Schloemer
• 1993 Jane Pegel
• 1994 Jane Pegel
• 1995 Jane Pegel
• 1996 Jane Pegel
• 2008 Chuck Lamphere
• 2009 F. Terrence Blanchard/Andy Burdick, skipper
• 2010 T Freytag
• 2011 F. Terrence Blanchard/Andy Burdick, skipper
• 2012 John Anderson/Vincent Porter, skipper
• 2013 Eagle, John R. Anderson/Vincent Porter, skipper
• 2014 Eagle, Ryan Fitzgerald /Vincent Porter, skipper
• 2015 Eagle, Ryan Fitzgerald/Vincent Porter, skipper
• 2016 Mad Cap, Thomas Freytag
• 2017 No Race
• 2018 TW Whowell, owner/RJ Porter, skipper
• 2019 No Race
• 2020 T Freytag
• 2021 Vincent Porter
• 2022 Vincent Porter
• 2023 Paul Reilly