A team from Curaçao won the first nine Caribbean championships, until 2010. The most recent champion of the region is a team from Curaçao. Curaçao's Pabao Little League won the 2004 Little League World Series, the only title to date for a Caribbean team.
The list below lists each country's participant in the Caribbean Little League Region Tournament. That year's winner is indicated in green.
Year | {{flagicon|ARU Aruba | {{flagicon|Antigua and Barbuda Antigua and Barbuda | {{flagicon|BAH Bahamas | {{flagicon|BER Bermuda | {{flagicon|Bonaire Bonaire | {{flagicon|BVI British Virgin Islands | {{flagicon|CAY Cayman Islands | {{flagicon|CUR Curaçao | {{flagicon|DOM Dominican Republic | {{flagicon|JAM Jamaica | {{flagicon|PUR Puerto Rico | {{flagicon|Sint Maarten Sint Maarten | {{flagicon|USVI U.S. Virgin Islands | Host |
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{{llwsy>2001}} | N/A Aruba | DNQ | N/A Bahamas | DNQ | DNQ | DNQ | DNQ | Pariba LL Willemstad | N/A Dominican Republic | DNQ | N/A Puerto Rico | N/A Sint Maarten | N/A U.S. Virgin Islands | None |
{{llwsy>2002}} | Aruba South LL Sint Nicolaas | DNQ | DNQ | DNQ | Bonaire LL Kralendijk | DNQ | DNQ | Pariba LL Willemstad | DNQ | DNQ | Adalberto Rodriguez LL Cabo Rojo | St. Maarten LL Philipsburg | Alvin McBean LL St. Thomas | | {{flagicon>USVI}} St. Croix
{{llwsy>2003}} | Aruba Central LL Santa Cruz | DNQ | Grand Bahamas Junior LL Freeport | DNQ | DNQ | BVI Little League Road Town | DNQ | Pabao LL Willemsted | Virgilio Jimenez LL Santo Domingo | DNQ | Rosario Y. Cardona LL Maunabo | St. Maarten LL Phillipsburg | Elmo Plaskett LL St. Croix | | {{flagicon>PUR}} Mayaguez
{{llwsy>2004}} | Aruba South LL Sint Nicolaas | DNQ | Grand Bahamas Junior LL Freeport | DNQ | Bonaire LL Kralendijk | BVI Little League Road Town | DNQ | Pabao LL Willemstad | Virgilio Jimenez LL Santo Domingo | DNQ | Jose M. Rodriguez LL Manatí | St. Maarten LL Philipsburg | Elrod Hendricks LL St. Thomas | | {{flagicon>ARU}} Oranjestad
2005 | Aruba North LL Oranjestad | DNQ | DNQ | DNQ | Bonaire LL Kralendijk | DNQ | DNQ | Pabao LL Willemstad | Antonio Irrizarry LL Puerto Plata | DNQ | Tati Lugo LL Yauco | St. Maarten LL Philipsburg | Elrod Hendricks LL St. Thomas | | {{flagicon>USVI}} St. Croix
2006 | Aruba North LL Oranjestad | DNQ | Freedom Farm LL Nassau | DNQ | Bonaire LL Kralendijk | DNQ | DNQ | Pabao LL Willemstad | Antonio Concepcion LL Moca | Bayside LL Kingston | Juan A. Bibiloni LL Yabucoa | St. Maarten LL Philipsburg | Elrod Hendricks West LL St. Thomas | | {{flagicon>PUR}} Vega Baja
2007 | Aruba North LL Oranjestad | DNQ | DNQ | DNQ | Bonaire LL Kralendijk | DNQ | DNQ | Pabao LL Willemstad | DNQ | Bayside LL Kingston | Tati Lugo LL Yauco | St. Maarten LL Philipsburg | Elrod Hendricks West LL St. Thomas | | {{flagicon>PUR}} Yabucoa
2008 | Aruba North LL Oranjestad | DNQ | DNQ | Bermuda Youth Athletic LL Southside | DNQ | DNQ | DNQ | Pabao LL Willemstad | Los Bravos de Pontenzuela LL Santiago | West Portland LL Portland | Juan Antonio Bibiloni LL Yabucoa | St. Maarten LL Philipsburg | Elrod Hendricks West LL St. Thomas | | {{flagicon>Bonaire}} Kralendijk
2009 | Aruba Central LL Santa Cruz | DNQ | DNQ | Bermuda Youth Athletic LL Southside | Bonaire LL Kralendijk | DNQ | DNQ | Pabao LL Willemstad | Los Bravos de Pontenzuela LL Santiago | DNQ | Radames Lopez LL Guayama | St. Maarten LL Philipsburg | Elmo Plaskett East LL St. Croix | | {{flagicon>CUR}} Willemstad
2010 | Aruba North LL Oranjestad | DNQ | DNQ | DNQ | Bonaire LL Kralendijk | DNQ | Grand Cayman Island LL George Town | Pariba LL Willemstad | Virgilio Jimenez LL Santo Domingo | DNQ | Jose M. Rodriguez LL Manatí | St. Maarten LL Philipsburg | Elmo Plaskett East LL St. Croix | | {{flagicon>PUR}} Humacao
2011 | Aruba North LL, Oranjestad Oranjestad | Antigua LL Saint John's | DNQ | DNQ | DNQ | DNQ | Cayman Islands LL Grand Cayman Island | Pariba LL Willemstad | José Tatis LL Puerto Plata | DNQ | Jose M. Rodriguez LL Manatí | St. Maarten LL Philipsburg | Elmo Plaskett East LL St. Croix
Elrod Hendricks West LL St. Thomas | | {{flagicon>USVI}} St. Thomas
2012 | Aruba Central LL Santa Cruz | Antigua LL Saint John's | DNQ | DNQ | DNQ | DNQ | DNQ | Pariba LL Willemstad | Solano LL San Pedro de Macorís | DNQ | Jose M. Rodriguez LL Manatí | St. Maarten LL Philipsburg | Elmo Plaskett East LL St. Croix
Elrod Hendricks West LL St. Thomas | | {{flagicon>PUR}} Guayama
2013 | Aruba Center LL Santa Cruz | DNQ | DNQ | DNQ | DNQ | DNQ | DNQ | Pariba LL Willemstad | DNQ | Jamaica LL | Samaritana LL San Lorenzo | St. Maarten LL Philipsburg | Elmo Plaskett East LL St. Croix
Elrod Hendricks West LL St. Thomas | | {{flagicon>Bonaire}} Kralendijk
2014 | Aruba North LL Oranjestad | DNQ | Freedom Farm LL Nassau | DNQ | Bonaire LL Kralendijk | DNQ | Cayman Islands LL George Town | Pabao LL Willemstad | Hector Delgado LL San Cristobal | DNQ | Miguel Luzunaris LL Humacao | DNQ | Elrod Hendrick West LL St. Thomas | | {{flagicon>Bahamas}} Freeport
2015 | Aruba Center LL Santa Cruz | DNQ | DNQ | DNQ | DNQ | DNQ | DNQ | Pabao LL Willemstad | Los Bravos de Pontezuela LL Santiago de los Caballeros | DNQ | Roberto Rivera Miranda LL Cayey | DNQ | Elrod Hendricks LL St. Thomas | | {{flagicon>CUR}} Willemstad
2016 | Aruba Center LL Santa Cruz | DNQ | DNQ | DNQ | Bonaire LL Kralendijk | DNQ | DNQ | Pariba LL Willemstad | La Javilla LL Santo Domingo | DNQ | Roberto Clemente LL Carolina | DNQ | Alvin McBean East LL St. Thomas | | {{flagicon>USVI}} St. Croix
2017 | Aruba, North LL, Noord | Antigua LL Saint John's | Unknown | DNQ | DNQ | DNQ | DNQ | Pariba LL Willemstad | Los Bravos de Pontezuela LL Santiago de los Caballeros | DNQ | Unknown | Unknown | Unknown St. Thomas | | {{flagicon>Antigua and Barbuda}} Saint John's
2018 | Aruba Center LL Santa Cruz | DNQ | Freedom Farm LL Nassau | DNQ | DNQ | DNQ | DNQ | Pabao LL Willemstad | Los Bravos de Pontezuela LL Santiago | DNQ | Radames Lopez LL Guayama | DNQ | Elmo Plaskett LL St. Thomas | | {{flagicon>Puerto Rico}}Sabana Grande