Every Caribbean Series Puerto Rico has won or hosted, from 1949 to today. Puerto Rico has won 16 Caribbean Series titles, most recently in 2018.
1951: Cangrejeros de Santurce won the Caribbean Series in Caracas, Venezuela.
1953: Cangrejeros de Santurce won the Caribbean Series in Havana, Cuba.
1954: Criollos de Caguas won the Caribbean Series in San Juan, Puerto Rico.
1955: Cangrejeros de Santurce won the Caribbean Series in Caracas, Venezuela. MVP: Don Zimmer.
1972: Leones de Ponce won the Caribbean Series in Santo Domingo, Dominican Republic.
1974: Criollos de Caguas won the Caribbean Series in Hermosillo, Mexico.
1975: Vaqueros de Bayamón won the Caribbean Series in San Juan, Puerto Rico.
1978: Indios de Mayagüez won the Caribbean Series in Mazatlán, Mexico.
1983: Lobos de Arecibo won the Caribbean Series in Caracas, Venezuela.
1987: Criollos de Caguas won the Caribbean Series in Hermosillo, Mexico.
1992: Indios de Mayagüez won the Caribbean Series in Hermosillo, Mexico.
1993: Cangrejeros de Santurce won the Caribbean Series in Mazatlán, Mexico.
1995: Senadores de San Juan won the Caribbean Series in San Juan, Puerto Rico.
2000: Cangrejeros de Santurce won the Caribbean Series in Santo Domingo, Dominican Republic.
2017: Criollos de Caguas won the Caribbean Series in Culiacán, Mexico.
2018: Criollos de Caguas won the Caribbean Series in Guadalajara, Mexico.