| Year | Skipper | Boat |
| 2001 | Bob Diehl | Diehler |
| 2002 | Robbins&Roser | Icon |
| 2003 | Johnson&Lynch | White Cloud |
| 2004 | Paul LaMarche | Neptune's Car |
| 2005 | Gray Hawken | Teddy Bear |
| 2006 | Bob Brunius | Time Bandit |
| 2007 | Dangerous When Striped | Chris Winnard |
| 2008 | Jay Platt | Fifth Season |
| 2009 | Bob Brunius | Time Bandit |
| 2010 | Daryl Homan | My Tai |
| 2011 | Carl Buchan | Madrona |