Grand Master
The Grand Masters trophy will be awarded to the highest placing skippers over the age of 65 in the A and B fleets at the Fleet 1 championships.
| Fleet | Year | Skipper |
| A | 2017 | Tucker Cheadle |
| 2016 | Argyle Campbell | |
| 2015 | Argyle Campbell | |
| 2014 | Argyle Campbell | |
| 2013 | Bob Yates | |
| 2012 | Tom Schock | |
| 2011 | Tom Schock | |
| 2010 | Tom Schock | |
| 2009 | Bob Yates | |
| 2008 | Lee Sutherland | |
| 2007 | Terry Gloege | |
| 2006 | Jim Kerrigan | |
| 2005 | Bob Yates | |
| B | 2017 | Pat Scruggs |
| 2016 | Tom Corkett | |
| 2015 | Tom Corkett | |
| 2014 | Tom Corkett | |
| 2013 | Win Fuller | |
| 2012 | Richard Blatterman | |
| 2011 | Win Fuller | |
| 2010 | Bill Allen | |
| 2009 | Rolly Pulaski | |
| 2008 | Ted Munroe | |
| 2007 | Kathy Sangster | |
| 2006 | Richard Blatterman | |
| 2005 | Glyn Davies | |
| C | 2017 | Kathy Sangster |
| 2016 | Rolly Pulaski | |
| 2015 | Dick Somers | |
| 2014 | Dick Somers |