The Dominican Republic has won the most Caribbean Series championships (23), with Tigres del Licey being the most successful team in the tournament's history.

The competition was the brainchild of Venezuelan baseball entrepreneur Pablo Morales and Oscar Prieto Ortiz, who devised the idea after seeing the success of the Serie Interamericana in 1946, which featured the clubs Brooklyn Bushwicks from the United States, Cervecería Caracas from Venezuela, Sultanes de Monterrey from Mexico, and an All-Star team composed of Cuban players.

[2] The representatives then agreed to stage a four-country, round-robin tournament 12-game to be known as the Serie del Caribe, to be launched in Cuba from February 20–25 of 1949.

Fidel Castro dissolved all professional baseball in Cuba, and MLB Commissioner Ford Frick ruled that American major leaguers were barred from playing in Havana, where the 1961 series had been scheduled.

[5] Starting with the 2013 Caribbean Series, a championship game was introduced where the two teams with the best win–loss record from the round-robin first stage would meet to determine the champion.