Caribbean Series (Serie del Caribe) champions 1949-2020
| YEAR | TEAM CITY | COUNTRY | MANAGER | RECORD | HOST COUNTRY |
|---|---|---|---|---|---|
| 1949 | Almendares | Cuba | Fermín Guerra | 6-0 | Cuba |
| 1950 | Carta Vieja | Panama | Wayne Blackburn | 5-2 | Puerto Rico |
| 1951 | Santurce | Puerto Rico | George Scales | 5-1 | Venezuela |
| 1952 | La Habana | Cuba | Mike González | 5-0 | Panamá |
| 1953 | Santurce | Puerto Rico | James Clarkson | 6-0 | Cuba |
| 1954 | Caguas | Puerto Rico | Mickey Owens | 4-2 | Puerto Rico |
| 1955 | Santurce | Puerto Rico | Herman Franks | 5-1 | Venezuela |
| 1956 | Cienfuegos | Cuba | Oscar Rodríguez | 5-1 | Panamá |
| 1957 | Marianao | Cuba | Napoleón Reyes | 5-1 | Cuba |
| 1958 | Marianao | Cuba | Napoleón Reyes | 4-2 | Puerto Rico |
| 1959 | Almendares | Cuba | Clemente Carreras | 5-1 | Venezuela |
| 1960 | Cienfuegos | Cuba | Antonio Castaños | 6-0 | Panamá |
| 1970 | Magallanes | Venezuela | Carlos Pascual | 7-1 | Venezuela |
| 1971 | Licey | Dominican Republic | Manuel Mota | 6-0 | Puerto Rico |
| 1972 | Ponce | Puerto Rico | Frank Verdi | 5-1 | Dominican Republic |
| 1973 | Licey | Dominican Republic | Tom Lasorda | 5-1 | Venezuela |
| 1974 | Caguas | Puerto Rico | Bobby Wayne | 4-2 | México |
| 1975 | Bayamón | Puerto Rico | José Pagán | 5-1 | Puerto Rico |
| 1976 | Hermosillo | Mexico | Benjamín Reyes | 5-1 | Dominican Republic |
| 1977 | Licey | Dominican Republic | Bob Rodgers | 6-0 | Venezuela |
| 1978 | Mayagüez | Puerto Rico | Rene Lachemann | 5-1 | México |
| 1979 | Magallanes | Venezuela | Willie Horton | 5-1 | Puerto Rico |
| 1980 | Licey | Dominican Republic | Del Crandall | 4-2 | Dominican Republic |
| 1981 | NO GAMES HELD | ||||
| 1982 | Caracas | Venezuela | Alfonso Carrasquel | 5-1 | México |
| 1983 | Arecibo | Puerto Rico | Ron Clark | 5-1 | Venezuela |
| 1984 | Zulia | Venezuela | Rubé Amaro, Sr. | 5-1 | Puerto Rico |
| 1985 | Licey | Dominican Republic | Terry Collins | 5-1 | México |
| 1986 | Mexicali | Mexico | Benjamín Reyes | 5-1 | Venezuela |
| 1987 | Caguas | Puerto Rico | Ramón Aviles | 5-2 | México |
| 1988 | Escogido | Dominican Republic | Phil Regan | 4-2 | Dominican Republic |
| 1989 | Zulia | Venezuela | Pete MacKanin | 5-1 | México |
| 1990 | Escogido | Dominican Republic | Felipe Rojas Alou | 5-1 | Miami |
| 1991 | Licey | Dominican Republic | John Roseboro | 5-0 | Miami |
| 1992 | Mayagüez | Puerto Rico | Pat Kelly | 5-2 | México |
| 1993 | Santurce | Puerto Rico | Mako Oliveras | 5-2 | México |
| 1994 | Licey | Dominican Republic | Casey Parsons | 5-1 | Venezuela |
| 1995 | San Juan | Puerto Rico | Luis Meléndez | 6-0 | Puerto Rico |
| 1996 | Culiacán | Mexico | Francisco Estrada | 5-1 | Dominican Republic |
| 1997 | Cibaeñas | Dominican Republic | Mike Quade | 4-2 | México |
| 1998 | Cibaeñas | Dominican Republic | Tony Peña | 6-0 | Venezuela |
| 1999 | Licey | Dominican Republic | Dave Jauss | 5-2 | Puerto Rico |
| 2000 | Santurce | Puerto Rico | Mako Oliveras | 6-0 | Dominican Republic |
| 2001 | Cibaeñas | Dominican Republic | Félix Fermín | 4-2 | México |
| 2002 | Culiacán | Mexico | Francisco Estrada | 5-1 | Venezuela |
| 2003 | Cibaeñas | Dominican Republic | Félix Fermín | 6-1 | Puerto Rico |
| 2004 | Licey | Dominican Republic | Manny Acta | 5-1 | Dominican Republic |
| 2005 | Mazatlán | Mexico | Juan José Pacho | 5-1 | México |
| 2006 | Caracas | Venezuela | Carlos Subero | 6-0 | Venezuela |
| 2007 | Cibaeñas | Dominican Republic | Félix Fermín | 5-1 | Puerto Rico |
| 2008 | Licey | Dominican Republic | Héctor de la Cruz | 5-1 | Dominican Republic |
| 2009 | Aragua | Venezuela | Buddy Bailey | 5-1 | México |
| 2010 | Escogido | Dominican Republic | Ken Oberkfell | 5-1 | Venezuela |
| 2011 | Obregón | México | Eddie Díaz | 4-2 | Puerto Rico |
| 2012 | Escogido | Dominican Republic | Ken Oberkfell | 4-2 | Dominican Republic |
| 2013 | Obregón | Mexico | Eddie Díaz | 4-3 | México |
| 2014 | Hermosillo | Mexico | Matías Carrillo | 4-2 | Venezuela |
| 2015 | Pinar del Río | Cuba | Alfonso Urguiola | 3-3 | Puerto Rico |
| 2016 | Mazatlan | Mexico | Juan Jose Pacho | 6-0 | Dominican Republic |
| 2017 | Caguas | Puerto Rico | Luis Matos | 3-3 | Mexico |
| 2018 | Caguas | Puerto Rico | Luis Matos | 4-2 | Mexico |
| 2019 | Herrera | Panama | Manuel Rodriguez | 4-1 | Panama |
| 2020 | La Romana | Dominican Republic | Lino Rivera | 6-1 | Puerto Rico |
