1999 Caribbean Series
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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
Final standings
| Country | Club | W | L | W/L % | Managers |
 Dominican Republic | Tigres del Licey * | 5 | 2 | .714 | Dave Jauss |
 Puerto Rico | Indios de Mayagüez | 4 | 3 | .571 | Al Newman |
.svg){kind=small} Venezuela | Cardenales de Lara | 2 | 4 | .333 | Omar Malavé |
 Mexico | Águilas de Mexicali | 2 | 4 | .333 | Francisco Estrada |
| * Won tie-breaking game for first place | |||||
Semifinals Dominican Republic vs Venezuela
1 2 3 4 5 6 7 8 9 R C H
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
1 2 3 4 5 6 7 8 9 10 R C H
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
Final
July 23, 1999 7:50 Dominican Republic vs Mexico
1 2 3 4 5 6 7 8 9
Tigres 0 1 0 2 0 0 0 0 4 Aguilas 0 1 0 2 0 0 2 0 X Tigres win 4:2