1999 Caribbean Cup
The Caribbean Cup, established in 1989, was the championship tournament for national association football teams that are members of the Caribbean Football Union.Preliminary round
Group A
| Team | | | | | | | |
| 4 | 2 | 1 | 1 | 0 | 3 | 0 |
| 2 | 2 | 0 | 2 | 0 | 2 | 2 |
| 1 | 2 | 0 | 1 | 1 | 2 | 5 |
----
----Group B
Group C
withdrew
----Group D
withdrew, leaving British Virgin Islands and Montserrat to compete.Group E
and both withdrew.Qualifying round
Group 1
| Team | | | | | | | |
| 9 | 3 | 3 | 0 | 0 | 13 | 2 |
| 6 | 3 | 2 | 0 | 1 | 11 | 3 |
| 3 | 3 | 1 | 0 | 2 | 6 | 9 |
| 0 | 3 | 0 | 0 | 3 | 1 | 17 |
----
----Group 2
| Team | | | | | | | |
| 9 | 3 | 3 | 0 | 0 | 4 | 1 |
| 6 | 3 | 2 | 0 | 1 | 5 | 2 |
| 1 | 3 | 0 | 1 | 2 | 2 | 5 |
| 1 | 3 | 0 | 1 | 2 | 2 | 5 |
----
----Group 3
| Team | | | | | | | |
| 6 | 3 | 2 | 0 | 1 | 9 | 8 |
| 4 | 3 | 1 | 1 | 1 | 8 | 7 |
| 4 | 3 | 1 | 1 | 1 | 7 | 7 |
| 3 | 3 | 1 | 0 | 2 | 4 | 6 |
----
----Group 4
| Team | | | | | | | |
| 9 | 3 | 3 | 0 | 0 | 12 | 0 |
| 4 | 3 | 1 | 1 | 1 | 5 | 6 |
| 4 | 3 | 1 | 1 | 1 | 2 | 4 |
| 0 | 3 | 0 | 0 | 3 | 0 | 9 |
----
----Group 5
withdrew
| Team | | | | | | | |
| 4 | 2 | 1 | 1 | 0 | 3 | 1 |
| 2 | 2 | 0 | 2 | 0 | 1 | 1 |
| 1 | 2 | 0 | 1 | 1 | 2 | 4 |
----
----Final tournament
Group 1
----
----Group 2
| Team | | | | | | | |
| 9 | 3 | 3 | 0 | 0 | 6 | 1 |
| 6 | 3 | 2 | 0 | 1 | 7 | 6 |
| 3 | 3 | 1 | 0 | 2 | 8 | 5 |
| 0 | 3 | 0 | 0 | 3 | 0 | 9 |
----
----Semi-Finals
----
The match was postponed from June 10 due to bad lighting.Third Place Match
The third place playoff was cancelled due to the condition of the field. Third place was shared between Jamaica and Haiti.Final
Result
Trinidad and Tobago qualified for the 2000 Gold CupAwards
Raciel Martinez
Ariel Álvarez
Clayton Ince
;Five goals
;Four goals
;Three goals
;Two goals
