| Award | Year | Fleet Captains | |
| Wednesday Night Racing | 1993 | Gerry Gayk | |
| Spring Series | 1994 | James May | |
| Summer Series | 1995 | Nancy Cybulski | |
| Fall Series | 1996 | Dianne Gustard | |
| 1997 | David Limoges | ||
| Weekend Distance Racing | 1998 | John Hemmingway | |
| Victoria Cup | 1999 | Bev Wilkshire | |
| Commodore's Cup | 2000 | Jay Bonnett | |
| THSC | 2001 | Jay Bonnett | |
| Pineapple Plate | 2002 | Jay Bonnett | |
| Island Race | 2003 | Corrine Caines | |
| Founders' Cup | 2004 | Brayden Woods | |
| Overall Champion | 2005 | Brayden Woods | |
| 2006 | Brayden Woods | ||
| Special Event Racing | 2007 | Jennifer Zimmerman | |
| Lady Skipper | 2008 | Jennifer Zimmerman | |
| Single-Handed | 2009 | Sean Furness | |
| Double-Handed | 2010 | Sean Furness | |
| Overnight | 2011 | Sheldon Street | |
| Last Blast | 2012 | Sheldon Street | |
| Other Awards | |||
| Most Improved | |||
| Broken Prop | |||
| Outstanding Member | |||
| Founders Award of Merit | |||
| Voyageur |
|
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