The Rosebowl events were held between 1966 and 1999.
Rosebowl (Northern Caribbean) Champions
| Year | Rosebowl Winner | Men's A | Men's B | Ladies | Veterans |
|---|---|---|---|---|---|
| 1999 | Jamaica | Jamaica | Jamaica | Jamaica | Jamaica |
| 1998 | Bermuda | Cayman | Bermuda | Bermuda | Bermuda |
| 1997 | Cayman | Cayman | Cayman | Cayman | Jamaica |
| 1996 | Jamaica | Cayman | Jamaica | Jamaica | Jamaica |
| 1995 | Jamaica | Bahamas | Jamaica | Cayman | Jamaica |
| 1994 | Bermuda | Cayman | Bermuda | Bermuda | Bermuda |
| 1993 | Jamaica | Cayman | Jamaica | Cayman | Jamaica |
| 1992 | Jamaica | Jamaica | Cayman | Jamaica | Jamaica |
| 1991 | Jamaica | Bahamas | Jamaica | Jamaica | Jamaica |
| 1990 | Jamaica | Bahamas | Jamaica | Jamaica | Jamaica |
| 1989 | Jamaica | Cayman | Jamaica | Jamaica | Jamaica |
| 1988 | Jamaica | Jamaica | Jamaica | Jamaica | Jamaica |
| 1987 | Bahamas | Bahamas | Bahamas | Bahamas | Bahamas |
| 1986 | Bermuda | Jamaica | Bermuda | Bermuda | Bahamas |
| 1985 | Jamaica | Jamaica | Jamaica | Jamaica | Bahamas |
| 1984 | Bahamas | Jamaica | Jamaica | Bahamas | Bahamas |
| 1983 | Jamaica | Jamaica | Jamaica | Bahamas | Bahamas |
| 1982 | Bermuda | Bermuda | Bermuda | Bermuda | Bahamas |
| 1981 | Jamaica | Bermuda | Jamaica | Jamaica | Nassau |
| 1980 | Bermuda | Bermuda | Jamaica | Jamaica | |
| 1979 | Bermuda | Bermuda | Bermuda | Bermuda | |
| 1978 | Bermuda | Bermuda | Bermuda | Bermuda | |
| 1977 | Jamaica | Jamaica | Nassau | Nassau | |
| 1976 | Jamaica | Jamaica | Jamaica | Jamaica | |
| 1975 | Bermuda | Bermuda | Bermuda | Bermuda | |
| 1974 | Jamaica | Jamaica | Jamaica | Jamaica | |
| 1973 | Bermuda | Bermuda | Jamaica | ||
| 1972 | Jamaica | Jamaica | Jamaica | ||
| 1971 | Freeport | Freeport | Freeport | ||
| 1970 | Bermuda | Bermuda | |||
| 1969 | Nassau | Nassau | |||
| 1968 | Bermuda | Bermuda | |||
| 1967 | Bermuda | ||||
| 1966 | Bermuda |