| 1st | 2nd | 3rd | |||||
| YEAR | DIVISION | SKIPPER | BOAT | SKIPPER | BOAT | SKIPPER | BOAT |
| 1995 | Warren Goodyear | October Wind | |||||
| 1996 | Robert Hayes | Whistling Duck | |||||
| 1997 | John Kupers | Dreamer | |||||
| 1998 | Robert Hayes | Whistling Duck | |||||
| 1999 | Robert Hayes | Whistling Duck | |||||
| 2000 | Robert Hayes | Whistling Duck | |||||
| 2001 | Brayden Woods | Daedalus | |||||
| 2002 | Division A | Graham Twomey | Jam | ||||
| Division B | Warren Goodyear | October Wind | |||||
| 2003 | Division A | Graham Twomey | Jam | ||||
| Division B | Warren Goodyear | October Wind | |||||
| 2004 | White Sail 1 | Bruce Patten | Irish Jig | ||||
| White Sail 2 | Dave Limoges | Nosko | |||||
| Spinnaker | Brayden Woods | Paladen | |||||
| 2005 | White Sail 1 | Raimond Rieder | Nebulous | ||||
| White Sail 2 | Dave Limoges | Nosko | |||||
| Spinnaker | Brayden Woods | Paladen | |||||
| 2006 | White Sail 1 | Dean Brown | Awesoma | ||||
| White Sail 2 | Michael Yarwood | Hawley | |||||
| Spinnaker | Brayden Woods | Paladen | |||||
| 2007 | White Sail 1 | Michael Delaney | Celtic Spirit | ||||
| White Sail 2 | John Kupers | California Girl | |||||
| Spinnaker | |||||||
| 2008 | White Sail 1 | Mitch Rothman | Rapture | ||||
| White Sail 2 | Cor Stapper | Cloud Dancer | |||||
| Spinnaker | Brayden Woods | Paladen | |||||
| 2009 | White Sail 1 | Sharon Neilson | Wyvern | John Plant | Watermark | Jay Bonnet | Skirtlifter |
| White Sail 2 | Dave Limoges | Nosko | Cor Stapper | Cloud Dancer | John Kupers | California Girl | |
| Spinnaker | Brayden Woods | Paladen | Dave Courtney | Better Still | Sean Furniss | Sierra Tango | |
| 2010 | White Sail 1 | Sharon Neilson | Wyvern | Willin | Dean Brown | Awesoma | |
| White Sail 2 | Bruce Patten | Irish Jig | Mike Yarwood | Hawley | Andrew Heim | Maroca II | |
| Spinnaker | Dave Courtney | Better Still | Jen Zimmerman | Ashe | Graham Twomey | Oz | |
| 2011 | White Sail 1 | Paul Kay | Clontarf | ||||
| White Sail 2 | Andrew Heim | Maroca II | |||||
| Spinnaker | Alex Kantemir | Byte Size | |||||
| 2012 | Spinnaker | Dave Courtney | Better Still | ||||
| White Sail 1 | Paul Kay | Clontarf | |||||
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