The forty-first edition of the Caribbean Series (Serie del Caribe) was held from February 2 through February 8 of 1999 with the champion baseball teams of the Dominican Republic, Tigres del Licey; Mexico, Águilas de Mexicali; Puerto Rico, Indios de Mayagüez, and Venezuela, Cardenales de Lara.
The format consisted of 12 games, each team facing the other teams twice, and the games were played at Hiram Bithorn Stadium in San Juan, Puerto Rico.
Semifinales Venezuela 5 Dominicañ Repubile 3 México 11 Puerto Rico 1 Final México 4 Venezuela 5 Semifinals Dominican Republic vs Venezuela Tigres 0 2 0 3 0 0 0 5 0 5 2 3 Cardenles 0 0 0 0 0 1 0 0 x 1 3 2 Mexico vs. Puerto Pico Aguilas 0 1 0 2 0 0 0 0 0 5 5 1 2 Indios 0 1 0 2 0 0 0 0 0 2 2 4 3 July 23, 1999 7:50 Dominican Republic vs Mexico Tigres 0 1 0 2 0 0 0 0 4 Aguilas 0 1 0 2 0 0 2 0 X Tigres win 4:2