This trophy was donated by the MBSA in 1973. Any high school with a sailing team may participate in this series.
| Year | School | A Team Captain | B Team Captain |
|
1973 |
Winthrop High |
J. Petrucci |
E. Corbett |
|
1974 |
Milton Academy |
F. Charles |
A. Rousmaniere |
|
1975 |
Weymouth North |
Jeffrey Kent |
Douglas Fowler |
|
1976 |
Cohasset High |
John Keane |
Brian Keane |
|
1977 |
Marblehead High |
J. Baxter |
N. & 1. Burke |
|
1978 |
Cohasset High |
Brian Keane |
John Keane |
|
1979 |
Cohasset High |
Brian Keane |
Ronald White |
|
1980 |
Dom Savio High |
Paul Clauss |
Gregory Dolan |
|
1981 |
Hingham High |
Russell Robinson |
David Ullrich |
|
1982 |
Hingham High |
David Ullrich |
Russell Robinson |
|
1983 |
Hingham High |
David Ulirich |
Tricia Moody |
|
1984 |
Brookline High |
Hartley Kelley |
Robert Rizika |
|
1985 |
Winchester High |
James Rowers |
Michael Bowers |
|
1986 |
Belmont High |
Tom Sitzman |
|
|
1987 |
Winchester High |
James Bouers |
Jon Burt |
|
1988 |
Belmont High |
Michael Mills |
Art Gleason |
|
1989 |
Belmont Hill |
Mike Mills |
|
|
1990 |
Belmont Hill |
Mike Huang |
|
|
1991 |
Belmont Hill |
Mike Huang |
|
|
1992 |
Belmont Hill |
Mike Huang |
|
|
1993 |
Belmont Hill |
Eli Galladuety |
Rich Canzano |
|
1994 |
Marblehead High |
Ramsey Key |
David Welch |
|
1995 |
Marblehead High |
David Welch |
Chris Gilman |
|
1996 |
Milton Academy |
Elizabeth Gill |
Hillary Drohan |
|
1997 |
Belmont Hill |
Todd Pastore |
Brad Yetman |
|
1998 |
Belmont Hill |
Thatcher Spring |
Ian Simonds |
|
1999 |
Manchester High |
Caleb Silsb |
Chris Pine |