Current
First awarded in 1991
Originally awarded to a yacht having an unplanned visit to Main Duck Island during the race, the trophy is an actual rock from Main Duck. With the advent of GPS, the original reason for awarding this trophy is a lot less relevant.
The trophy was re-assigned starting in 2003 to the winner of the Double Handed Spinnaker Division-2 of the LO300
| 1991 | Hal Seaman | |
| 1992 | Bubele Hut | Hidebrand, Phillip |
| 1993 | Conspicuous | W Eddy, K Graham |
| 1994 | Sumo | D Toogood, J Bangay |
The trophy was re-assigned starting in 2003 to the winner of the Double Handed Spinnaker 2 division. LO300.
| 2003 | Southerly Buster | Roger Shaw |
| 2004 | Not Awarded | |
| 2005 | Restless | Joe Rosenfeld & Matthew Richter, KYC |
| 2006 | Taliesin | Michael Innell, CBYC |
| 2007 | Vitesse | Bob Fields, S. Jarosz, RYC |
| 2008 | Heartbreaker | Michael Judd, D. Leonard, BHYC |
| 2009 | Heartbreaker | Michael Judd, D. Leonard, BHYC |
| 2010 | Les | John Hagen, Gerrt Docherty, EYC |