The 1949 Caribbean Series was the first edition of the Caribbean Series. It was held from February 20 through February 25 with the champion baseball teams of Cuba, Alacranes del Almendares; Panama, Spur Cola Colonites; Puerto Rico, Indios de Mayagüez and Venezuela, Cervecería Caracas.
The second edition of the Caribbean Series was held from February 21 through February 27, in 1950. It featured the champion baseball teams of Cuba, Alacranes del Almendares; Panama, Carta Vieja Yankees; Puerto Rico, Criollos de Caguas, and Venezuela, Navegantes del Magallanes. The format consisted of 12 games, each team facing the other teams twice, and the games were played at Sixto Escobar Stadium in San Juan, Puerto Rico.
The fourth edition of the Caribbean Series was played in 1952. It was held from February 20 through February 26, featuring the champion baseball teams of Cuba, Leones del Habana; Panama, Carta Vieja Yankees; Puerto Rico, Senadores de San Juan and Venezuela, Cervecería Caracas. The format consisted of 12 games, each team facing the other teams twice, and the games were played at Panama City. The first pitch was thrown by Alcibíades Arosemena, by then the President of Panama.
The twelfth edition of the Caribbean Series was a baseball tournament held from February 10 through February 15, 1960 featuring the champion teams from Cuba (Cienfuegos), Panama (Marlboro), Puerto Rico (Caguas) and Venezuela (Rapiños). The format consisted of 12 games, each team facing the other teams twice, and the games were played at Estadio Nacional of Panama City.
After nine years of absence, the thirteenth edition of the Caribbean Series was revived in 1970 without the representing baseball clubs of Cuba and Panama. It was held in Caracas, Venezuela from February 5 to February 10 at Estadio Universitario, featuring the original members of the first stage. Puerto Rico was represented by the Leones de Ponce, while the host Navegantes del Magallanes represented Venezuela. The Dominican Republic debuted in the Series and was represented by the Tigres del Licey to complete a three-team tournament. The format consisted of 12 games, with each team facing the other competitors three times. Because the series was so small, each team had to face each other in one night.
The seventh edition of the Caribbean Series was played in 1955. It was held from February 10 through February 15, featuring the champion baseball teams from Cuba, Alacranes de Almendares; Panama, Carta Vieja Yankees; Puerto Rico, Cangrejeros de Santurce, and Venezuela, Navegantes del Magallanes. The format consisted of 12 games, each team facing the other teams twice. The games were played at Estadio Universitario in Caracas, the capital city of Venezuela, which boosted capacity to 22,690 seats, while the ceremonial first pitch was thrown by Marcos Pérez Jiménez, by then the President of Venezuela.
The ninth edition of the Caribbean Series was played in 1957. It was held from February 9 through February 14, featuring the champion baseball teams of Cuba, Tigres de Marianao; Panama, Cerveza Balboa; Puerto Rico, Indios de Mayagüez, and Venezuela, Leones del Caracas. The format consisted of 12 games, each team facing the other teams twice. The games were played at Estadio del Cerro in Havana, the Cuban capital. The first pitch was thrown by Ford Frick, by then the Commissioner of Major League Baseball.
After a year of absence, the twenty-fourth edition of Baseball's Caribbean Series finally took place in 1982. It was held from February 4 through February 9 with the champions teams from Dominican Republic, Leones del Escogido; Mexico, Naranjeros de Hermosillo; Puerto Rico, Leones de Ponce and Venezuela, Leones del Caracas. The format consisted of 12 games, each team facing the other teams twice. The games were played at Héctor Espino Stadium in Hermosillo, Mexico, which boosted capacity to 16.000 seats.
The eighth edition of the Caribbean Series was played in 1956. It was held from February 10 through February 15, featuring the champion baseball teams of Cuba, Elefantes de Cienfuegos; Panama, Chesterfield Smokers; Puerto Rico, Criollos de Caguas and Venezuela, Industriales de Valencia. The format consisted of 12 games, each team facing the other teams twice. The games were played at Estadio Olímpico de Panamá in Panama City, Panama.
The fifth edition of the Caribbean Series was played in 1953. It was held from February 20 through February 25, featuring the champion baseball teams of Cuba, Leones de la Habana; Panama, Chesterfield Smokers; Puerto Rico, Cangrejeros de Santurce, and Venezuela, Leones del Caracas. The format consisted of 12 games, each team facing the other teams twice. The games were played at Estadio del Cerro in Havana, the Cuban capital.
The sixth edition of the Caribbean Series was played in 1954. It was held from February 18 through February 23, featuring the champion baseball teams from Cuba, Panama, Puerto Rico ,(Criollos de Caguas) and Venezuela. Lácteos de Pastora were the champion of the Liga Occidental de Béisbol Profesional rather than the Venezuelan Professional Baseball League. The format consisted of 12 games, each team facing the other teams twice. The games were played at Estadio Sixto Escobar in San Juan, P.R.
The tenth edition of the Caribbean Series was played in 1958. It was held from February 8 through February 13 with the champions teams from Cuba, Tigres de Marianao; Panama, Carta Vieja Yankees; Puerto Rico, Criollos de Caguas and Venezuela, Industriales de Valencia. The format consisted of 12 games, each team facing the other teams twice. The games were played at Estadio Sixto Escobar in San Juan, Puerto Rico.
The eleventh edition of the Caribbean Series was played in 1959. It was held from February 10 through February 15 with the champions teams from Cuba (Almendares), Panama (Coclé), Puerto Rico (Santurce) and Venezuela (Oriente). The format consisted of 12 games, each team facing the other teams twice. The games were played at UCV Stadium in Caracas, Venezuela, which boosted capacity to 35.000 seats, and the first pitch was thrown by Edgar Sanabria, by then the President of Venezuela.
The twenty-third edition of the Caribbean Series was played in 1980. It was held from February 2 through February 7 with the champions teams from Dominican Republic, Mexico, Puerto Rico and Venezuela. The format consisted of 12 games, each team facing the other teams twice. The games were played at Estadio Quisqueya in Santo Domingo, D.R., which boosted capacity to 14.000 seats, and the first pitch was thrown by Antonio Guzmán, by then the President of Dominican Republic.
The twenty-sixth edition of the Caribbean Series was played in 1984. It was held from February 4 through February 9 with the champion teams from Dominican Republic, Mexico, Puerto Rico and Venezuela. The format consisted of 12 games, each team facing the other teams twice. The games were played at Hiram Bithorn Stadium in San Juan, Puerto Rico.
The twenty-seventh edition of the Caribbean Series of baseball was played in 1985. It was held from February 2 through February 7 with the champion teams from Dominican Republic, Mexico, Puerto Rico and Venezuela. The format consisted of 12 games, each team facing the other teams twice. The games were played at Estadio Teodoro Mariscal in Mazatlán, Mexico.
The sixteenth edition of the Caribbean Series was played in 1973. It was held from February 1 through February 6 with the champions teams from Dominican Republic, Mexico, Puerto Rico and Venezuela. The format consisted of 12 games, each team facing the other teams twice, and the games were played at UCV Stadium in Caracas, Venezuela. The Series was played to honor the memory of Roberto Clemente, who died on December 31, 1972, during a humanitarian mission to assist victims of the 1972 Nicaragua earthquake.
The eighteenth edition of the Caribbean Series was played in 1975. It was held from February 1 through February 6 with the champions teams from the Dominican Republic, Águilas Cibaeñas; Mexico, Naranjeros de Hermosillo; Puerto Rico, Vaqueros de Bayamón and Venezuela, Tigres de Aragua. The format consisted of 12 games, each team facing the other teams twice, and was played at Hiram Bithorn Stadium in San Juan, Puerto Rico. For the first time in Series history, the designated hitter was adopted following the implementation of this rule by the American League during the 1973 MLB season.
The nineteenth edition of the Caribbean Series was played in 1976. It was held from February 4 through February 9 with the champions teams from the Dominican Republic, Águilas Cibaeñas; Mexico, Naranjeros de Hermosillo; Puerto Rico, Vaqueros de Bayamón and Venezuela, Tigres de Aragua. The format consisted of 12 games, each team facing the other teams twice, and was played in Dominican Republic. For the first time in Series history, the games were played at two different venues, the Estadio Quisqueya in Santo Domingo and the Estadio Cibao in Santiago de los Caballeros.
The twentieth edition of the Caribbean Series was played in 1977. It was held from February 4 through February 9 with the champions teams from the Dominican Republic, Tigres del Licey; Mexico, Venados de Mazatlán; Puerto Rico, Criollos de Caguas and Venezuela, Navegantes del Magallanes. The format consisted of 12 games, each team facing the other teams twice, and the games were played at UCV Stadium in Caracas, Venezuela.
Cangrejeros de Santurce (1st title)
Leones del Habana 
