| 1st | 2nd | 3rd | |||||
| YEAR | DIVISION | SKIPPER | BOAT | SKIPPER | BOAT | SKIPPER | BOAT |
| 1998 | Peter Reothy | Waterman | |||||
| 1999 | Anssi Kairo | Dreamer | |||||
| 2000 | |||||||
| 2001 | Graham Twomey | Jam | |||||
| 2002 | John Kupers | Sweet Sixteen | |||||
| 2003 | single handed | Warren Goodyear | October Wind | ||||
| White Sail 1 | Brayden Woods | Paladen | |||||
| White Sail 2 | Bruce Patten | Irish Jig | |||||
| Cruising | Plato Routis | Slow Dancer | |||||
| 2004 | single handed | Warren Goodyear | October Wind | ||||
| White Sail 1 | Stewart Rauch | Pax | |||||
| White Sail 2 | Frank Vanzon | SubtleWaves | |||||
| Spinnaker | Tom Lacqement | Ravenscroft | |||||
| 2005 | single handed | David Courtney | Better Still | ||||
| White Sail 1 | Bruce Patten | Irish Jig | |||||
| Spinnaker | Brayden Woods | Paladen | |||||
| 2006 | single handed | David Courtney | Better Still | ||||
| White Sail 1 | Alexander Kantemir | Abegweit | |||||
| White Sail 2 | John Kupers | California Girl | |||||
| Spinnaker | Brayden Woods | Paladen | |||||
| 2007 | White Sail 1 | Alexander Kantemir | Abegweit | ||||
| 2008 | White Sail 2 | John Kupers | California Girl | ||||
| 2009 | Single Handed | Dave Courtney | Better Still | Mike Yarwood | Hawley | ||
| White Sail | John Kupers | California Girl | Alex Kantemir | Byte Size | Irish Jig | ||
| Spinnaker | Sean Furniss | Sierra Tango | Lady Windy | ||||
| 2010 | White Sail 2 | John Kupers | California Girl | ||||
| Spinnaker | Brayden Woods | Paladen | Jen Zimmerman | Ashe | Alex Kantemir | Byte Size | |
| 2011 | White Sail 2 | Paul Kay | Clontarf | ||||
| Spinnaker | Brayden Woods | Paladen | |||||
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