| Caribbean Series Champions |
| Year |
Winner |
| 1949 |
Cuba (Almendares) |
| 1950 |
Panama (Carta Vieja) |
| 1951 |
Puerto Rico (Santurce) |
| 1952 |
Cuba (La Habana) |
| 1953 |
Puerto Rico (Santurce) |
| 1954 |
Puerto Rico (Caguas) |
| 1955 |
Puerto Rico (Santurce) |
| 1956 |
Cuba (Cienfuegos) |
| 1957 |
Cuba (Marianao) |
| 1958 |
Cuba (Marianao) |
| 1959 |
Cuba (Almendares) |
| 1960 |
Cuba (Cienfuegos) |
| 1961 |
No Series |
| 1962 |
No Series |
| 1963 |
No Series |
| 1964 |
No Series |
| 1965 |
No Series |
| 1966 |
No Series |
| 1967 |
No Series |
| 1968 |
No Series |
| 1969 |
No Series |
| 1970 |
Venezuela (Magallanes) |
| 1971 |
Dominican Republic (Licey) |
| 1972 |
Puerto Rico (Ponce) |
| 1973 |
Dominican Republic (Licey) |
| 1974 |
Puerto Rico (Caguas) |
| 1975 |
Puerto Rico (Bayamon) |
| 1976 |
Mexico (Hermosillo) |
| 1977 |
Dominican Republic (Licey) |
| 1978 |
Puerto Rico (Mayaguez) |
| 1979 |
Venezuela (Magallanes) |
| 1980 |
Dominican Republic (Licey) |
| 1981 |
No Series |
| 1982 |
Venezuela (Caracas) |
| 1983 |
Puerto Rico (Arecibo) |
| 1984 |
Venezuela (Zulia) |
| 1985 |
Dominican Republic (Licey) |
| 1986 |
Mexico (Mexicali) |
| 1987 |
Venezuela (Caguas) |
| 1988 |
Dominican Republic (Escogido) |
| 1989 |
Venezuela (Zulia) |
| 1990 |
Dominican Republic (Escogido) |
| 1991 |
Dominican Republic (Licey) |
| 1992 |
Puerto Rico (Mayaguez) |
| 1993 |
Puerto Rico (Mayaguez) |
| 1994 |
Dominican Republic (Licey) |
| 1995 |
Puerto Rico (San Juan) |
| 1996 |
Mexico (Culicun) |
| 1997 |
Dominican Republic (Aguilas) |
| 1998 |
Dominican Republic (Aguilas) |
| 1999 |
Dominican Republic (Licey) |
| 2000 |
Puerto Rico (Santurce) |
| 2001 |
Dominican Republic (Aguilas) |
| 2002 |
Mexico (Culicun) |
| 2003 |
Dominican Republic (Aguilas) |
| 2004 |
Dominican Republic (Licey) |
| 2005 |
Mexico (Mazatlan) |
