Caracas hosted the Caribbean Series for the second time in 1955, and the Cangrejeros de Santurce returned to claim another championship, giving Puerto Rico its third title in three years — a stretch of dominance that had no precedent in the young tournament. The Cangrejeros were carrying a roster assembled with considerable care during this era of Puerto Rican winter baseball, and their consistency across multiple editions of the Series reflected an organization operating at a high level. Bob Thurman was recognized as the edition's Most Valuable Player, though his specific role in that designation is not on record in a way that allows detailed characterization. Some details of this edition remain unverified. What is known is that Thurman's recognition added an individual award to what was already a team achievement of considerable note. Three consecutive Puerto Rican championships represented the longest winning streak any single nation had produced in the Series to that point, and they came at a time when the tournament was still building its own traditions.
Champion: Cangrejeros de Santurce · Country: Puerto Rico · Host: Caracas, Venezuela · MVP: Don Zimmer
It was the 3rd Caribbean Series title for Cangrejeros de Santurce and the 4th for Puerto Rico, which has won 16 in all. Caracas hosted the tournament for the 2nd time.
The 1954 edition was won by Criollos de Caguas in San Juan. Elefantes de Cienfuegos took the 1956 title in Caracas.