| Overall | |||||||
| YEAR | DIVISION | SKIPPER | BOAT | ||||
| 1998 | Robert Hayes | Whistling Duck | |||||
| 1999 | Robert Hayes | Whistling Duck | |||||
| 2000 | Robert Hayes | Whistling Duck | |||||
| 2001 | Warren Goodyear | October Wind | |||||
| 2002 | Warren Goodyear | October Wind | |||||
| 2003 | Warren Goodyear | October Wind | |||||
| 2004 | White Sail 1 | Bruce Patten | Irish Jig | ||||
| White Sail 2 | John Kupers | Dreamer | |||||
| Spinnaker | Brayden Woods | Paladen | |||||
| 2005 | White Sail 1 | Raimond Rieder | Nebulous | ||||
| White Sail 2 | Evan Karaim | Going My Way | |||||
| Spinnaker | Dave Courtney | Better Still | |||||
| 2006 | White Sail 1 | Raimond Rieder | Nebulous | ||||
| White Sail 2 | John Kupers | California Girl | |||||
| Spinnaker | Brayden Woods | Paladen | |||||
| 2007 | White Sail 1 | Michael Delaney | Celtic Spirit | ||||
| White Sail 2 | |||||||
| Spinnaker | |||||||
| 2008 | White Sail 1 | Mitch Rothman | Rapture | ||||
| White Sail 2 | |||||||
| Spinnaker | |||||||
| Spring | Summer | Fall | |||||
| 2009 | White Sail 1 | Sharon Neilson | Wyvern | Dean Brown | Awesoma | John Plant | Watermark |
| White Sail 2 | Dave Limoges | Nosko | Dave Limoges | Nosko | Dave Limoges | Nosko | |
| Spinnaker | Brayden Woods | Paladen | Dave Courtney | Better Still | Brayden Woods | Paladen | |
| 2010 | White Sail 1 | ||||||
| White Sail 2 | |||||||
| Spinnaker | |||||||
| Overall | Alex Kantemir | Byte Size | Dave Courtney | Better Still | Mike Yarwoord | Hawley | |
| 2011 | White Sail 1 | ||||||
| White Sail 2 | |||||||
| Spinnaker | |||||||
| 2012 | No Race | ||||||
|
Lakeshore Yacht Club 2013 Hosted by Netsell.com, contact Dean Brown, |