Panama City hosted the Caribbean Series for the second time in 1956, and the championship returned to Cuba through the Cienfuegos club. The result ended Puerto Rico's three-year run of dominance and reasserted the competitive presence of Cuban winter baseball in the regional forum. Cienfuegos was one of several Havana-area clubs that cycled through Caribbean Series competition during the founding era, and their title in Panama City added to the accumulating record of Cuban success in the tournament. Camilo Pascual, pitching for Cienfuegos, was named the Most Valuable Player — a recognition that reflected his stature as one of the more accomplished arms of his generation. Pascual would go on to a distinguished major league career, but his MVP performance in Panama City came during his formative years and offered an early signal of the ability that would define him. Some details of this edition carry a degree of uncertainty, but his designation as the top pitcher of the tournament is part of the established record.
Champion: Elefantes de Cienfuegos · Country: Cuba · Host: Caracas, Venezuela · MVP: Camilo Pascual (Pitcher)
It was the 1st Caribbean Series title for Elefantes de Cienfuegos and the 3rd for Cuba, which has won 8 in all. Caracas hosted the tournament for the 3rd time.
The 1955 edition was won by Cangrejeros de Santurce in Caracas. Tigres de Marianao took the 1957 title in Havana.