San Juan hosted the Caribbean Series in 1999, and the Dominican Republic's Tigres del Licey claimed the championship with a 5-2 record, with Puerto Rico's Indios de Mayagüez finishing as runner-up. The title added to Licey's unmatched collection of Caribbean Series championships.
Champion: Tigres del Licey · Country: Dominican Republic · Host: San Juan, Puerto Rico
It was the 8th Caribbean Series title for Tigres del Licey and the 12th for Dominican Republic, which has won 23 in all. San Juan hosted the tournament for the 9th time.
The 1998 edition was won by Águilas Cibaeñas in Puerto La Cruz. Cangrejeros de Santurce took the 2000 title in Santo Domingo.