Originally for the Enterprise fleet, later awarded to the best Enterprise in the handicap fleet.
| Year | Sail Number | Class | Helm & Crew |
|---|---|---|---|
| 2000 | 21822 | B & L Cumming | |
| 1999 | 21822 | B & L Cumming | |
| 1998 | 21822 | B & L Cumming | |
| 1997 | 21822 | B & L Cumming | |
| 1996 | 22150 | P&E Dolling | |
| 1995 | 22150 | P&E Dolling | |
| 1994 | 21822 | B & L Cumming | |
| 1993 | 22322 | S&D Fisher | |
| 1992 | 20628 | R Mant | |
| 1991 | 21822 | B & L Cumming | |
| 1990 | 21822 | B & L Cumming | |
| 1989 | 21822 | B & L Cumming | |
| 1988 | 20538 | B & L Cumming | |
| 1987 | 20538 | B & L Cumming | |
| 1986 | 20538 | B & L Cumming | |
| 1985 | 20538 | B & L Cumming | |
| 1984 | 19698 | J Jarvis | |
| 1983 | 19750 | R & J mason | |
| 1982 | 19750 | R & J mason | |
| 1981 | 19750 | R & J mason | |
| 1980 | 14820 | B & L Cumming | |
| 1979 | 19455 | J Jarvis | |
| 1978 | 19455 | J Jarvis | |
| 1977 | 1857 | J Balderson | |
| 1976 | 10245 | I Drinkwater | |
| 1975 | 1857 | J Balderson | |
| 1974 | 1857 | J Balderson | |
| 1973 | 1857 | J Balderson | |
| 1972 | 8537 | J Burland |