The fiftieth edition of the Caribbean Series (Serie del Caribe) was played in . It was held from February 2 through February 7, featuring the champions teams from Mexico, Yaquis de Obregón; Venezuela, Tigres de Aragua, and two teams from Dominican Republic: Águilas Cibaeñas [1] and Tigres del Licey [2]. The format consisted of 12 games, each team facing the other teams twice, and was played at Estadio Cibao, home of the Águilas. Licey finished second in the Dominican League, but made the Series due to the cancellation of the Puerto Rican League season due to financial problems. It was the first Series fully held in the city of Santiago de los Caballeros and the first round-robin of its kind to feature two teams from the Dominican Republic.
Licey, managed by Héctor de la Cruz, finished with a 5–1 record to clinch the club's 10th Caribbean Series title since the country began participating in 1970 and the 17th overall for the Dominican Republic. Pitcher and Series MVP Ramón Ortiz posted a 2–0 record with a 0.00 ERA in scoreless IP against the Águilas, including five of relief. RF Nelson Cruz provided the offensive support for the team, leading the Series hitters in batting average (.407), hits (11), doubles (3), SLG (.630) and OPS (1,037). Licey also got fine work off starters José Capellán (1-0, 3.37 ERA) and Francisco Rosario (0.00, five SO in 6.0 IP), as well from relievers Jailen Peguero (1-0) and Carlos Mármol (two saves). Other contributions came from 3B/OF José Bautista (.250, two home runs, four RBI, six runs, two stolen bases, .440 SLG), 2B Ronnie Belliard (.273 BA, four RBI, .455 SLG), LF Emilio Bonifacio (.250, five runs, two SB) and C Matt Tupman, who batted .364 (8-for-23) and was the only of Licey's players with at least one hit in each game.
Managed by Félix Fermín, the Dominican champions wasted home field advantage, ending in second place with a 3–3 mark. The Cibao's team was characterized by an ineffective pitching staff and a poor offense, while the defense committed crucial errors. Two hitters carried much of the offensive weight – 2B Rafael Furcal (.400, 10 hits, five runs, four RBI, .560 SLG) and SS Tony Peña Jr. (.429 BA, .524 SLG), while DH Miguel Tejada provided a substantial (if discreet) contribution (.208, five runs, two HR, .318 SLG). Pitchers Joselo Díaz (1-0, eight strikeouts, 1.50 ERA in six IP) and Arnie Muñoz (1-0, one save, 0.00 in IP) headed the staff. Supporting them were Randy Choate (0.00 ERA, 4.0 IP), Joel Peralta (0.00, 2.0 IP) and Francisco Cruceta (1.69, IP), but Denny Bautista (1-0), Bartolo Colón (0-1), Sergio Ramírez and Alfredo Simón, combined for an 8.00 ERA in 18 innings.
Mexico was guided by Homar Rojas and finished with a 2–4 record, tying for third place with Venezuela. DH Robert Saucedo (.346, seven runs, six RBI, .577 SLG), SS Alfredo Amézaga (.381, five runs, three SB, .435 OBP) and OF Armando Ríos (.312, two SB, .375 SLG) paced the offense, while the top pitcher was Nelson Figueroa (1-0, 0.81, seven SO in 11.0 IP). The Obregón team also included players like Justin Lehr (P), Óscar Robles (2B), Dan Serafini (P) and Reggie Taylor (OF).
Venezuela, piloted by Buddy Bailey, played with a depleted line-up. This year, 15 players from the Venezuelan finals roster were unavailable for the Series, including Miguel Cabrera, Ronny Cedeño and Edgardo Alfonzo, due to Spring Training reports. Luis Maza, the man charged with filling Cabrera's shoes at third base, responded by hitting .348 (8-for-23) with six runs and a .435 SLG. Other help came from outfielders Selwyn Langaigne (.357, four RBI) and Alberto Callaspo (.346, four runs), as well from pitchers Giovanni Carrara (1-0, four hits, four SO, 0.00 ERA in 5.0 IP) and Ramón García (three hits, three SO, 0.00 ERA in 4.0 IP). The only homers were hit by sub-batters Alex Delgado (C, .100) and Luis Ugueto (OF, .222), while Andrew Lorraine was the only pitcher to lose two games in the Series that year. The Aragua club also featured RF Robert Pérez and pitchers Orber Moreno, Víctor Moreno and José Santiago, among others.
Of 33 players on the Series rosters included on the 40-man Major League 2008 rosters, 30 were on the Dominican Republic teams. According to MLB, the Caribbean Confederation officials considered moving up the start of the 2009 tournament from the first week of February to the last week of January, because it gives the players at least 10 days before they are expected to report to their respective camps in Spring Training. This year's tournament ended six days before pitchers and catchers begin reporting. The change would encourage more participation for major leaguers from Mexico, Dominican Republic, Puerto Rico and Venezuela. Adding new teams to the tournament could also be an option for the future of the Caribbean Series.
| Country | Club | W | L | W/L % | GB | Managers |
| 5 | 1 | .833 | – | |||
| 3 | 3 | .500 | 2.0 | |||
| 2 | 4 | .333 | 3.0 | |||
| 2 | 4 | .333 | 3.0 | |||
| Individual leaders | |||||
| Player/Club | Statistic | ||||
| .407 | |||||
| Home runs | 2 | ||||
| 6 | |||||
| 7 | |||||
| 11 | |||||
| 3 | |||||
| 1 | |||||
| Stolen bases | 3 | ||||
| .483 | |||||
| .630 | |||||
| 1.037 | |||||
| 2 | |||||
| Strikeouts | 8 | ||||
| 0.00 | |||||
| 2 | |||||
| 4 | |||||
| Awards | |||||
| Most Valuable Player | |||||
| All-Star Team | |||||
| Name/Club | Position | ||||
| catcher | |||||
| first baseman | |||||
| second baseman | |||||
| third baseman | |||||
| shortstop | |||||
| left fielder | |||||
| center fielder | |||||
| right fielder | |||||
| designated hitter | |||||
| RH pitcher | |||||
| LH pitcher | |||||
| manager | |||||