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Philip J. Roosevelt Trophy
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The Pleon Yacht Club was honored during its Fiftieth Anniversary Year, 1937, with an invitation from the Seawanhaka Corinthian Yacht Club of New York to compete in an annual series of Junior Team Races between Massachusetts Bay and Long Island Sound for a trophy offered by Philip J. Roosevelt, president of the North American Yacht Racing Union. 

These annual team races between the Pleon Yacht Club and the Seawanhaka Corinthian Junior Yacht Club are to be sailed alternately at Oyster Bay and Marblehead, commencing in 1938 on Long Island Sound. The conditions require three crews of two juniors each, of the Sears Cup age, with the option of racing more crews to a side by mutual consent, and the series is sailed in a suitable junior class of the home club. If possible, each match shall consist of a complete round robin using the change-of-boat system, and the winner of the match is determined on the aggregate total score.

THE WINNERS

1938 Seawanhaka Corinthian
1939 Pleon
1940 Seawanhaka Corinthian
1941 Pleon
1942 Pleon
1943-1945 No Competition
1946 Pleon
1947 Pleon
1948 Pleon
1949 Seawanhaka Corinthian
1950 Pleon
1951 Seawanhaka Corinthian
1952 Pleon
1953 Pleon
1954-1955 No Competition
1956 Pleon
1957 Series Incomplete
1958 Pleon
1959 Seawanhaka Corinthian
1961 Seawanhaka Corinthian
1962 Pleon
1963 Pleon
1964 Pleon
1965 Seawanhaka Corinthian
1966 Pleon
1967-1998 No Competition
1999 Pleon
2000 Seawanhaka Corinthian
2001 Pleon
2002 Pleon
2003 No Competition
2004 No Competition

2005 No Competition

2006 No Competition

2007 No Competition 

2008 No Competition

2009 No Competition

2010 No Competition