Havana hosted the Caribbean Series for the third time in 1957, and it was Puerto Rico's Criollos de Caguas who claimed the championship, defeating the Cuban clubs on their own ground for the second time in the decade. The Criollos had previously won in San Juan in 1954, and their 1957 title in Havana demonstrated a consistent ability to compete at the highest level of Caribbean winter baseball regardless of venue. It was the fourth Puerto Rican championship in the tournament's nine-year history. No Most Valuable Player was formally recorded for this edition, and some details remain unverified. The Criollos' success in Havana nonetheless carried weight beyond its place in the standings. Cuba's capital remained the symbolic center of Caribbean baseball during this period, and a visiting club claiming the title there spoke to the genuine depth of talent that Puerto Rican winter baseball had developed across the founding decade. The 1957 edition also came just two years before significant political upheaval would begin reshaping the Cuban baseball landscape.
Champion: Tigres de Marianao · Country: Cuba · Host: Havana, Cuba
It was the 1st Caribbean Series title for Tigres de Marianao and the 4th for Cuba, which has won 8 in all. Havana hosted the tournament for the 3rd time.
The 1956 edition was won by Elefantes de Cienfuegos in Caracas. Tigres de Marianao took the 1958 title in San Juan.