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.
Summary
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.png.webp){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
Individual leaders
| Player | Statistic | ||||
| Batting | |||||
| Carlos Mendoza (VEN) | Batting average | .529 | |||
| Ferdinand Rodríguez (PUR) | Runs | 9 | |||
| Neifi Pérez (DOM) | Hits | 12 | |||
| Wes Chamberlain (VEN) Ferdinand Rodríguez (PUR) | Home runs | 3 | |||
| David Ortiz (DOM) | RBI | 9 | |||
| Four players tied | Stolen bases | 2 | |||
| Pitching | |||||
| Anthony Chavez (DOM) | Wins | 2 | |||
| José Rosado (PUR) | Strikeouts | 13 | |||
| José Rosado (PUR) | ERA | 0.77 | |||
| José Rosado (PUR) | Innings pitched | 11.2 | |||
| Miguel Alicea (PUR) | Saves | 3 | |||
All-Star team
| 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) | Manager | ||||
Sources
- Bjarkman, Peter. Diamonds around the Globe: The Encyclopedia of International Baseball. Greenwood. ISBN 978-0-313-32268-6
- Serie del Caribe : History, Records and Statistics (Spanish)
- Resumen de la Serie del Caribe 1999 (Spanish)
- Tigres del Licey : Una mirada histórica a la Serie del Caribe (Spanish)