The first Caribbean Series was held in Havana in February 1949, and from the outset it carried the weight of a genuine regional championship. Four nations sent their winter-league representatives — Cuba, Panama, Puerto Rico, and Venezuela — and it was Cuba's own Almendares that emerged as the inaugural champion, doing so on home soil. The tournament established a round-robin format that would define the competition for its founding era, and Havana's role as host gave the event an immediate sense of permanence and civic pride. Agapito Mayor was named the Series' first Most Valuable Player, finishing with a perfect 3-0 record on the mound. His performance gave Almendares the kind of pitching backbone that championship teams require, and his name became the first written into the tournament's record book. The selection of a pitcher as the inaugural MVP signaled something about how the competition was won in those early years: arms, not just bats, decided things. Havana 1949 was the foundation upon which eleven more pre-suspension editions would be built.
Champion: Alacranes del Almendares · Country: Cuba · Host: Havana, Cuba · MVP: Agapito Mayor (Pitcher (3-0)) · Manager: Miguel Ángel González
It was the 1st Caribbean Series title for Alacranes del Almendares and the 1st for Cuba, which has won 8 in all.
Carta Vieja Yankees took the 1950 title in San Juan.