San Juan hosted the Caribbean Series for the third time in 1958, and the championship went to Marianao, a Cuban club that had not previously claimed a regional title in the tournament. Cuba reasserted itself on the Series stage in Puerto Rico, interrupting what might otherwise have been a sustained period of Puerto Rican home-field advantage at this venue. Marianao's title added variety to the list of Cuban champions in the founding era, reflecting the depth that existed across multiple clubs within the Cuban winter circuit. No Most Valuable Player was officially recorded for this edition, and some details of the competition remain unverified. The 1958 edition was held at a moment of growing political tension in Cuba, though the tournament itself proceeded as a sporting event. With hindsight, it was one of the final editions before the Cuban Revolution began reshaping the relationship between Cuban baseball and the rest of the Caribbean, a process that would ultimately lead to the suspension of the entire tournament from 1961 through 1969.
Champion: Tigres de Marianao · Country: Cuba · Host: San Juan, Puerto Rico
It was the 2nd Caribbean Series title for Tigres de Marianao and the 5th for Cuba, which has won 8 in all. San Juan hosted the tournament for the 3rd time.
The 1957 edition was won by Tigres de Marianao in Havana. Alacranes del Almendares took the 1959 title in Caracas.