The Mount Gay Trophy is named for long time sponsor and provider of those Red Hats.
First presented in 1989, since 2007 it has been awarded to the yacht with the Best Corrected Time in the Multihull Fleet.
| 1989 | Gunnersmate II | J. Harvey, OYS |
| 1990 | Gunnersmate II | J. Harvey, OYS |
| 1991 | Gunnersmate II | J. Harvey, OYS |
| 1992 | Gunnersmate II | J. Harvey, OYS |
| 1993 | Conspicuous | W. Eddy, |
| 1994 | Gunnersmate II | J. Harvey, OYS |
| 2007 | Triumphant | D. Fice, WGYC |
| 2008 | Flight Simulator | Tom Reese, YYC |
| 2009 | Triumphant | D. Fice, IYC |
| 2010 | Flight Simulator | Tom Reese, YYC |


Current
