Skipper's Choice Regatta History
| Year | Boat Number | Boat Name | 1st Place Skipper | 1st Place Crew | 2nd Place | 3rd Place |
|---|
| 2006 | | | | | | |
| 2005 | | not sailed | | | | |
| 2004 | | not sailed | | | | |
| 2003 | 7621 | Owl | Ross Weene | Peter Costa | Josh Matteson | Eric Larsen |
| 2002 | 7468 | Turnip Truck | Erik Goethert | John Siljander | Greg Reuter | Chris Anto |
| 2001 | 6767 | Foxy | Mark Lindsay | John Fox | Will Welles | Peter Rodriques |
| 2000 | 7621 | Owl | Jim Mullane | Peter Costa | Dave Fortier | Ted Grossbart |
| 1999 | 7782 | Stiletto | Russell Robinson | Kurt Larson | Dave Hickey | John Murphy |
| 1998 | 7782 | Stiletto | Barry Lawton | Kurt Larson | Philip Marks | Tommy May |
Boston Harbor Star Fleet
