Current
Awarded jointly to the winners of the Spinnaker and Main & Jib divisions in the Directors Race. First offered in 1990 for a race or series of races on weekend days to encourage participation in longer point-to-point racing.
| 1990 (Spinnaker) | Dark & Stormy | Bob Clark |
| 1990 (Main & Jib) | Winsome 11 | Derrick Plummer |
| 1990 (Novice) | Wayward | J Wilkinson |
| 1991 (Spinnaker) | Dark & Stormy | Bob Clark |
| 1991 (Main & Jib) | Tiercel 11 | Don Cooper |
| 1992 (Spinnaker) | Dark & Stormy | Bob Clark |
| 1992 (Spinnaker) | Adam Bomb | Adam Farcas |
| 1992 (Main & Jib) | Patent Pending | Dennis Moss |
| 1993 (Spinnaker) | Dark & Stormy | Bob Clark |
| 1993 (Main & Jib) | Tenacity Too | George Wentlandt |
| 1994 (Spinnaker) | Adam Bomb | Adam Farkas |
| 1994 (Main & Jib) | Fast Busy | Glen Richardson |
| 1995 (Main & Jib) | Undecided | Paul Norgard |
| 1995 (Spinnaker) | Adam Bomb | Adam Farkas |
| 1996 (Spinnaker) | Tango | Rudy Wolfs |
| 1996 (Main & Jib) | Blade Runner | Peter Wolfe |
| 1997 (Main & Jib) | Hang 50 | C Scott |
| 1997 (Spinnaker) | Folichon | Ian McAllister |
| 1998 (Spinnaker) | Riot Act | S Lingard |
| 1998 (Main & Jib) | Hustler | R Henderson |
| 2000 (Spinnaker) | Folichon | Ian McAllister |
| 2000 (Spinnaker) | Storm Boy | Mike Conner |
| 2000 (Spinnaker) | Kick-a-Little | Mark Searle |
| 2001 (Spinnaker) | Flak | Adam Farkas |
| 2001 (Main & Jib) | Soca | Bill Stewart |
| 2002 (Spinnaker) | Rex | S. Weakley / S.Panagiotidis |
| 2002 (Main & Jib) | Folichon | Ian McAllister |
| 2003 (Spinnaker) | Sentient | Bill Rourke |
| 2003 (Main & Jib) | Folichon | Ian McAllister |
| 2004 (Main & Jib only) | Nick’s Café | Pat Muise |
| 2005 (Main & Jib) | Sea Jay | Jim Johnstorne |
| 2005 (Spinnaker) | Sentient | Bill Rourke |
| 2006(Main & Jib) | Bear Necessity | Dexter Halsal |
| 2006 (Spinnaker) | Defiant II | Bob Bugbee |
| 2007 (Main & Jib) | Epiphany | Ron Smallbone |
| 2007 (Spinnaker) | Folichon | Ian McAllister |
| 2008 (Main & Jib) | Wayward | Jim Wilkinson |
| 2008 (Spinnaker) | Gizmo | Marc Doedens |
| 2009(Main & Jib) | Wayward | Jim Wilkinson |
| 2009 (Spinnaker) | Gizmo | Marc Doedens |
| 2010 (Spinnaker) | Folichon | Brian Townsend |
| 2010 (White Sail) | Storm Boy | Michael O’Connor |