The 1959 Caribbean Series was held in Caracas, and Cuba's Almendares claimed the championship — the same club that had won the inaugural edition a decade earlier in Havana. Venezuela hosted the penultimate edition before the long suspension, and Almendares' title gave the tournament's founding decade a sense of symmetry, bookending ten years of competition with the same Cuban franchise. No Most Valuable Player is on record for this edition, and some details remain subject to verification. The 1959 Series was played in a year of extraordinary change in Cuba: the Revolution had taken power in January, and its long-term consequences for Cuban professional baseball were beginning to take shape, though the full impact would not be felt immediately. Almendares' championship in Caracas was, in retrospect, one of the final acts of the pre-revolutionary Cuban baseball order on the Caribbean Series stage. The suspension that would follow in 1961 made this edition, and the one that came after, part of an unrepeatable closing chapter.
Champion: Alacranes del Almendares · Country: Cuba · Host: Caracas, Venezuela
It was the 2nd Caribbean Series title for Alacranes del Almendares and the 6th for Cuba, which has won 8 in all. Caracas hosted the tournament for the 4th time.
The 1958 edition was won by Tigres de Marianao in San Juan. Elefantes de Cienfuegos took the 1960 title in Panama City.