Clean-up Trophy
Awarded annually to the yacht with the highest Corrected Time Average Speed for combined Spring and Fall Races. Donated by co-founder, Charles F. Dickerson, to the yacht in his words “who polished his bottom the most”. The highest Corrected Time Average Speed is calculated by dividing the sum of the distances for the two races by the sum of the two corrected times.
| 1956 | Whisker | John R. Fales |
| 1957 | Povanne | R. Read Shaw |
| 1958 | Necton | Charles Dickerson |
| 1959 | Mabubay | Breckenridge Marshall |
| 1960 | Melita | W. Sayles Nicholson |
| 1961 | Volta | John Nicholas Brown |
| 1962 | Suzy | Herman Wyss, Jr. |
| 1963-64 | Tango | Ernest H. McVay |
| 1965 | Shady Lady | G. Richard Westin |
| 1966 | Marango | Adelbert A. Goff |
| 1967-68 | Little Nell | Richard C. Philbrick |
| 1969 | Nepenthe | Robert W. Read |
| 1970 | Mahi Mahi | William H. Shaw |
| 1971 | The Golden Fleece | John A. Dickerson |
| 1972 | Floating Bear | Julian Gibbs |
| 1973 | Conquest | Avery Seaman |
| 1974 | Vamoose | W. Donald Wilson |
| 1975 | Keewaydin | Ken Welter |
| 1976 | Caneel | Chip Hawkins |
| 1977 | Vamoose | W. Donald Wilson |
| 1978-79 | Sugarfoot | John Westbrook |
| 1980 | Petrel | Julian Gibbs |
| 1981 | Super Splurge | Dean Mathews |
| 1982 | Banshee | Bob Almeida |
| 1983 | Skal | Gordon Hagglund |
| 1984 | No Award Given | |
| 1985 | Nepenthe | Robert W. Read |
| 1986 | Queequeg | Nathaniel Nazareth |
| 1987 | Scratch | Jeff Spranger |
| 1988 | Rowse-ta-bout | Tom Rowse |
| 1989 | Priscilla | Roger Coutu |
| 1990 | Panama Red | Richard Bioty |
| 1991 | Rigadoon | Bill Riggs |
| 1992-93 | Dirty Harry | John Lavin |
| 1994 | Expresso | Peter Manickas |
| 1995 | Mon Keill | Robert Cassity |
| 1996 | Beth | Steven Sammis |
| 1997 | Scratch | Jeff Spranger |
| 1998 | Cover Girl | Ralph Kinder |
| 1999 | Wind Ensemble | Dennis Stoops |
| 2000 | Kima | Nelson Weiderman |
| 2001 | Blue Heron | Peter Northrup |
| 2002 | Nepenthe | Robert Read |
| 2003 | Kima | Nelson Weiderman |
| 2004 | R’Buoy | John Brady |
| 2005 | Polaris | Peter Northup |
| 2006 | Polaris | Peter Northup |
| 2007 | Petrel | Jonathan Gibbs |
| 2008 | Coconut | Tom D’Albora |
| 2009 | Coconut | Tom D’Albora |
| 2010 | Coconut | Tom D’Albora |
| 2011 | Coconut | Tom D’Albora |
| 2012 | Rigadoon | Bill & Doug Riggs |
| 2013 | Rigadoon | Bill & Doug Riggs |
| 2014 | Coconut | Tom D’Albora |
| 2015 | Coconut | Tom D’Albora |
| 2016 | Spirit | EC Helme |
| 2017 | Two Dogs | Moose McClintock |
| 2018 | Mischief | David Schwartz |
| 2019 | Salacia | Mark Nannini |
| 2020 | Serendipity | Gary Venable |