| 1st | 2nd | 3rd | |||||
| YEAR | DIVISION | SKIPPER | BOAT | SKIPPER | BOAT | SKIPPER | BOAT |
| 1996 | Gary Manning | Darina VI | |||||
| 1997 | John Kupers | Dreamer | |||||
| 1998 | |||||||
| 1999 | |||||||
| 2000 | David Courtney | Better Still | |||||
| 2001 | Warren Goodyear | October Wind | |||||
| 2002 | Division A | Gerald Roloson | Karma | ||||
| Division B | Warren Goodyear | October Wind | |||||
| 2003 | Division A | Tom Lacquement | Ravenscroft | ||||
| Division B | Robert Hayes | Popsicle Stick | |||||
| Cruising Division | Judy Preston | Andante ll | |||||
| 2004 | White Sail 1 | Warren Goodyear | October Wind | ||||
| White Sail 2 | Michael Yarwood | Hawley | |||||
| Spinnaker | Brayden Woods | Paladen | |||||
| 2005 | White Sail 1 | Raimond Rieder | Nebulous | ||||
| White Sail 2 | Evan Karaim | Going My Way | |||||
| Spinnaker | Brayden Woods | Paladen | |||||
| 2006 | White Sail 1 | Judy Preston | Andante ll | ||||
| White Sail 2 | Cor Strapper | Cloud Dancer | |||||
| Spinnaker | Jim Wilkinson | Foxpaw | |||||
| 2007 | White Sail 1 | ||||||
| White Sail 2 | |||||||
| Spinnaker | Jen Zimmerman | Ashe | |||||
| 2008 | White Sail 1 | ||||||
| White Sail 2 | |||||||
| Spinnaker | Sean Furniss | Sierra Tango | |||||
| 2009 | White Sail 1 | Judy Preston | Andante II | ||||
| White Sail 2 | Bruce Patton | Irish Jig | |||||
| Spinnaker | Sean Furniss | Sierra Tango | |||||
| 2010 | White Sail 1 | Skirtlifter | Judy Preston | Andante II | Union Jack | ||
| White Sail 2 | Bruce Patton | Irish Jig | Kristina | ||||
| Spinnaker | Alex Kantemir | Byte Size | Sean Furniss | Sierra Tango | Jen Zimmerman | Ashe | |
| 2011 | White Sail 1 | Kristina | |||||
| White Sail 2 | |||||||
| Spinnaker | |||||||
| 2012 | Tal Wolf | Critical Path | |||||
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