The forty-first edition of the Caribbean Series (Serie del Caribe) was held from February 2 through February 8 of 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 5Dominicañ Repubile 3México 11Puerto Rico 1
Final México 4Venezuela 5
| Country | Club | W | L | W/L % | Managers |
| Tigres del Licey * | 5 | 2 | .714 | Dave Jauss | |
| 4 | 3 | .571 | Al Newman | ||
| 2 | 4 | .333 | Omar Malavé | ||
| 2 | 4 | .333 | Francisco Estrada | ||
| * Won tie-breaking game for first place | |||||
1 2 3 4 5 6 7 8 9 R C HTigres 0 2 0 3 0 0 0 5 0 5 2 3Cardenles 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 HAguilas 0 1 0 2 0 0 0 0 0 5 5 1 2Indios 0 1 0 2 0 0 0 0 0 2 2 4 3
Final July 23, 1999 7:50Dominican Republic vs Mexico 1 2 3 4 5 6 7 8 9Tigres 0 1 0 2 0 0 0 0 4Aguilas 0 1 0 2 0 0 2 0 X Tigres win 4:2
| Player | Statistic | ||||
| Batting | |||||
| Carlos Mendoza (VEN) | .529 | ||||
| Ferdinand Rodríguez (PUR) | 9 | ||||
| Neifi Pérez (DOM) | 12 | ||||
| Wes Chamberlain (VEN) Ferdinand Rodríguez (PUR) | Home runs | 3 | |||
| David Ortiz (DOM) | 9 | ||||
| Four players tied | Stolen bases | 2 | |||
| Pitching | |||||
| Anthony Chavez (DOM) | 2 | ||||
| José Rosado (PUR) | Strikeouts | 13 | |||
| José Rosado (PUR) | 0.77 | ||||
| José Rosado (PUR) | 11.2 | ||||
| Miguel Alicea (PUR) | 3 | ||||
| Name | Position | ||||
| Henry Mercedes (DOM) | Catcher | ||||
| Wes Chamberlain (VEN) | First baseman | ||||
| Ever Magallanes (MEX) | Second baseman | ||||
| Edwards Guzmán (PUR) | Third baseman | ||||
| Neifi Pérez (DOM) | Shortstop | ||||
| Darryl Brinkley (MEX) | Left fielder | ||||
| Manny Martínez (DOM) | Center fielder | ||||
| Karim García (MEX) | Right fielder | ||||
| Luis Polonia (DOM) | Designated hitter | ||||
| Miguel Batista (DOM) | Right-handed pitcher | ||||
| José Rosado (PUR) | Left-handed pitcher | ||||
| Miguel Alicea (PUR) | Relief pitcher | ||||
| Awards | |||||
| Neifi Pérez (DOM) | Most Valuable Player | ||||
| Dave Jauss (DOM) | |||||