| Year: | 1999 |
| Other Titles: | Copa Caribe 1999 |
| Country: | Trinidad and Tobago |
| Num Teams: | 27 |
| Confederations: | 2 |
| Finalists: | 8 |
| Champion: | Trinidad and Tobago |
| Count: | 7 |
| Second: | Cuba |
| Top Scorer: |  Ariel Álvarez(5 goals) |
| Player: | Raciel Martinez |
| Prevseason: | 1998 |
| Nextseason: | 2001 |
The Caribbean Cup, established in 1989, was the championship tournament for national association football teams that are members of the Caribbean Football Union.
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withdrew----
withdrew, leaving British Virgin Islands and Montserrat to compete.
and both withdrew.
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Saint-Martin withdrew
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The match was postponed from June 10 due to bad lighting.
The third place playoff was cancelled due to the condition of the field. Third place was shared between Jamaica and Haiti.
Trinidad and Tobago qualified for the 2000 Gold Cup
Raciel Martinez
Ariel Álvarez (five goals)
Luis Marten
Damas-Agis Patrice