Secretary's Cup History
| Year | Boat Number | Boat Name | 1st Place Skipper | 1st Place Crew | 2nd Place | 3rd Place |
|---|
| 2007 | 8245 | Brillo 40k | Joe Zambella | Dan Vannoni | Braverman | MacDonald |
| 2006 | | | | | | |
| 2005 | 7629 | | Ken Woods | Howard Davis | Zambella | Costa |
| 2004 | 8052 | Don't Look Back | Stephen Braverman | Cindy Olsen | Rosen | Charles |
| 2003 | 8052 | Don't Look Back | Cindy Olsen | Stephen Braverman | | |
| 2002 | 7324 | Southern Cross | Jake Fiumara | Joe Chambers | | |
| 2001 | 7732 | Night Light | Gary MacDonald | Howard Davis | Fox | Braverman |
| 2000 | 7621 | Owl | Peter Costa | Jessica Costa | Charles | Trotsky |
| 1999 | 7728 | Hayaku | John Lombard | Mike Whitford | Sustronk | Bainton |
| 1998 | 7804 | Night Light | Gary MacDonald | Sergey Leonidov | Braverman | Charles |
| 1997 | | | | | | |
| 1996 | 7168 | Eclair | Jay Spaulding | | Woods | Brown |
| 1995 | 7728 | Stars & Snipes | Ron Sandstrom | Brett James | Vessella | MacDonald |
| 1994 | | | | | | |
| 1993 | 7681 | Erin | John MacCausland | Eric Beckwith | | |
| 1992 | 7324 | Rosebud Cafe | John Safford | Joe Chambers | | |
| 1991 | | not sailed | | | | |
| 1990 | | not sailed | | | | |
| 1989 | 7349 | Owl | Peter Costa | Chris Lanza | | |
| 1988 | 6911 | Night Light | Gary MacDonald | Dave Winkler | | |
| 1987 | 7265 | | John MacCausland | Bob MacCausland | | |
| 1986 | 6984 | Decoy | Bear Hovey | Neil Foley | | |
| 1985 | | not sailed | | | | |
| 1984 | 6523 | Brillo | Joe Zambella | | | |
| 1983 | 6523 | Brillo | Joe Zambella | Leo Dawson | | |
| 1982 | 6523 | Brillo | Joe Zambella | Leo Dawson | | |
Boston Harbor Star Fleet
