Little League World Series (Caribbean Region) Regional championship Regional championship

| Year_ | Aruba | Bahamas | Bermuda | Bonaire | British_Virgin_Islands | Cayman_Islands | Curaçao | Dominican_Republic | Jamaica | Puerto_Rico | Sint_Maarten | U_S_Virgin_Islands | Host_ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 2006 | Aruba North LL Oranjestad | 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 | Jaime Collazo LL Vega Baja |
| 2007 | Aruba North LL Oranjestad | 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 | Juan A. Bibiloni LL Yabucoa |
| 2008 | Aruba North LL Oranjestad | 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 | Bonaire LL Kralendijk |
| 2009 | Aruba Central LL Santa Cruz | 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 | Willemstad LL Willemstad |