1^st Caribbean Series (1949): Held in Habana, Cuba. Almendares, managed by Fermin Guerra represented Cuba. Spur Cola with Cubans Orlando Moreno and Leonardo Goicochea represented Panama. Indios de Mayaguez represented Puerto Rico, Spur Cola represented Panama and Cerveceria Caracas represented Venezuela. Almendares went 6-0 to win the inaugural series. Agapito Mayor won three games and Monte Irvin led in HRs and RBIs.

2^nd Caribbean Series (1950): Held in San Juan, Puerto Rico, from February 21 to 27, 1950. Almendares represented Cuba. On the roster where Cuban stars Santos Amaro, Avelino Canizares, Andres Fleitas, Fermin Guerra (Catcher/Manager), Conrado Marrero, Willie Miranda, Rene Montegeagudo and Hector Rodriguez. Magallanes Navegantes represented Venezuela with Cuban catcher Gilverto "Chino" Valdivia and pitcher Santiago Ulrich. Caguas Criollos represented Puerto Rico and Carta Vieja represented Panama. Panama won the series and Hector Rodriguez was the leading batter with a .473 average.

3rd Caribbean Series (1951): Held in Caracas, Venezuela. Habana represented Cuba. Managed by Miguel Angel Habana had Cuban stars Edmundo Amoros, Chiquitin Cabrera and Pedro Formental. Magallanes Navegantes, who was managed by Cuban Lazaro Salazar, represented Venezuela. Santurce's Cangrejeros and represented Puerto Rico and Spur Cola represented Panama. Puerto Rico (5-1) won the series with Cuba (4-2) in second. Chiquitin Cabrera led hitters with a .619 average and Rene Gonzalez, with Magallanes, led in RBI.

4th Caribbean Series (1952): Held in Panama City, Panama. Habana, managed by Miguel Angel Gonzalez represented Cuba. Edmundo Amoros, Pedro Formental and Pitcher Tom Fine, who pitched the first no hitter in Caribbean Series history, led Habana. Cerveceria Caracas represented Venezuela, Carta Vieja represented Panama and San Juan represented Puerto Rico. Amoros won the batting title with a .450 average and Cuba won the series with a 5-0-1 record.

5th Caribbean Series (1953): Held in Habana, Cuba. Habana, managed by Miguel Angel Gonzalez represented Cuba. Edmundo Amoros and Pedro Formental, series best hitter (.560), led Habana. Cerveceria Caracas, managed by Martin Dihigo represented Venezuela. Panama, represented by Chesterfield, had Cuban Roberto Tapanez at first. Puerto Rico was represented by a strong Santurce's Cangrejeros team, which won the series.

6th Caribbean Series (1954): Held in San Juan, Puerto Rico. Almendares represented Cuba. Pastora, managed by Napoleon Reyes represented Venezuela. Puerto Rico was represented by Caguas' Criollos, which won the series. Carta Vieja represented Panama. The highlight for the Cubans was a shutout pitched by Conrado Marrero against a strong Panamanian team.

7th Caribbean Series (1955): Held in Caracas, Venezuela. Almendares represented Cuba. Magallanes Navegantes, managed by Lazaro Salazar represented Venezuela. Carta Vieja represented Panama. Puerto Rico was represented by Santurce Cangrejeros, which won the series. The Puerto Rican team is considered the strongest in Caribbean Series history with the likes of Willie Mays and Roberto Clemente. It would be Puerto Rico's last win in this phase of the series. Don Zimmer led in HRs, Almendares' Rocky Nelson in hitting, Willie Mays in RBIs and Roberto Clemente in runs scored.

8th Caribbean Series (1956): Held in Panama City, Panama. Cuba was represented by Cienfuegos, which won with a 5-1 record. Venezuela was represented by Valencia Industriales, managed by Regino Otero, coached by Reinaldo Cordeiro and with Elio and Pelayo Chacon, jr. in the Outfield. Puerto Rico was represented by Caguas Criollos. Rafael Noble led in hitting with  .400 avg. and Humberto "Chico" Fernandez in runs scored. Camilo Pascual and Pedro Ramos each won two games.

9th Caribbean Series (1957): Held in Habana, Cuba. Cuba was represented by Marianao and managed by Napoleon Reyes. Marianao won with a 5-1 record. Mayaguez Indians represented Puerto Rico, Caracas reresented Venezuela and Balboa reresented Panama. Minnie Minoso tied for the lead in RBIs. It was also Conrado Marrero, who was 46, last hurrah as a player.

10th Caribbean Series (1958): Held in San Juan, Puerto Rico. Cuba was represented by Marianao and managed by Napoleon Reyes. Marianao won again with a 4-2 record. Venezuela was represented by Valencia Industriales and managed by Regino Otero. Carta Vieja represented Panama and Puerto Rico was represented by Caguas Criollos with Clemente.

11th Caribbean Series (1959): Held in Caracas, Venezuela. Almendares, who added Camilo Pascual to its already loaded roster, represented Cuba. Marianao won again with a 4-2 record. Oriente who had Elio Chacon represented Venezuela. Cocle represented Panama and Santurce's Cangrejeros with Orlando Cepeda represented Puerto Rico. The overpowering Cuban pitching staff included Camilo Pascual, Orlando Pena and Mike Cuellar.

12th Caribbean Series (1960): Held in Panama City, Panama. Cienfuegos, managed by Tony Castano represented Cuba. Cienfuegos won with a 6-0 record. Rapinos with Luis Aparicio represented Venezuela. Marlboro represented Panama and Puerto Rico was represented by Caguas Criollos with Orlando Cepeda. Camilo Pascual won two games including a shutout against Puerto Rico. In addition Raul Sanchez, Pedro Ramos and Orlando Pena also won games.

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