| Copa Caribe 1999 | |
|---|---|
| Tournament details | |
| Host country | Trinidad and Tobago |
| Teams | 27 (from 2 confederations) |
| Final positions | |
| Champions |  Trinidad and Tobago (7th title) |
| Runners-up |  Cuba |
| Tournament statistics | |
| Top scorer(s) | Ariel Álvarez (5 goals) |
| Best player(s) | Raciel Martinez |
The Caribbean Cup, established in 1989, was the championship tournament for national association football teams that are members of the Caribbean Football Union.
| Team | Pld | W | D | L | GF | GA | GD | Pts |
|---|---|---|---|---|---|---|---|---|
 Bahamas | 2 | 1 | 1 | 0 | 3 | 0 | +3 | 4 |
 U.S. Virgin Islands | 2 | 0 | 2 | 0 | 2 | 2 | 0 | 2 |
 Turks and Caicos Islands | 2 | 0 | 1 | 1 | 2 | 5 | −3 | 1 |
French Guiana withdrew
Anguilla withdrew, leaving British Virgin Islands and Montserrat to compete.
Aruba and 
Sint Maarten both withdrew.
| Team | Pld | W | D | L | GF | GA | GD | Pts |
|---|---|---|---|---|---|---|---|---|
| Cuba | 3 | 3 | 0 | 0 | 13 | 2 | +11 | 9 |
 Bermuda | 3 | 2 | 0 | 1 | 11 | 3 | +8 | 6 |
 Cayman Islands | 3 | 1 | 0 | 2 | 6 | 9 | −3 | 3 |
| Bahamas | 3 | 0 | 0 | 3 | 1 | 17 | −16 | 0 |
| Bermuda | 4–1 | Cayman Islands |
|---|---|---|
Smith  Boyles | Brown |
| Cayman Islands | 4 - 1 | Bahamas |
|---|---|---|
| Whittaker Brown Dinnall |
| Team | Pld | W | D | L | GF | GA | GD | Pts |
|---|---|---|---|---|---|---|---|---|
 Guadeloupe | 3 | 3 | 0 | 0 | 4 | 1 | +3 | 9 |
 Barbados | 3 | 2 | 0 | 1 | 5 | 2 | +3 | 6 |
 Antigua and Barbuda | 3 | 0 | 1 | 2 | 2 | 5 | −3 | 1 |
 Dominica | 3 | 0 | 1 | 2 | 2 | 5 | −3 | 1 |
| Team | Pld | W | D | L | GF | GA | GD | Pts |
|---|---|---|---|---|---|---|---|---|
 Saint Kitts and Nevis | 3 | 2 | 0 | 1 | 9 | 8 | +1 | 6 |
 Saint Lucia | 3 | 1 | 1 | 1 | 8 | 7 | +1 | 4 |
 Saint Vincent and the Grenadines | 3 | 1 | 1 | 1 | 7 | 7 | 0 | 4 |
 Martinique | 3 | 1 | 0 | 2 | 4 | 6 | −2 | 3 |
| Team | Pld | W | D | L | GF | GA | GD | Pts |
|---|---|---|---|---|---|---|---|---|
 Haiti | 3 | 3 | 0 | 0 | 12 | 0 | +12 | 9 |
 British Virgin Islands | 3 | 1 | 1 | 1 | 5 | 6 | −1 | 4 |
 Dominican Republic | 3 | 1 | 1 | 1 | 2 | 4 | −2 | 4 |
 Puerto Rico | 3 | 0 | 0 | 3 | 0 | 9 | −9 | 0 |
| Haiti | 2–0 | Puerto Rico |
|---|---|---|
Saint-Martin withdrew
| Team | Pld | W | D | L | GF | GA | GD | Pts |
|---|---|---|---|---|---|---|---|---|
 Grenada | 2 | 1 | 1 | 0 | 3 | 1 | +2 | 4 |
 Suriname | 2 | 0 | 2 | 0 | 1 | 1 | 0 | 2 |
 Netherlands Antilles | 2 | 0 | 1 | 1 | 2 | 4 | −2 | 1 |
| Team | Pld | W | D | L | GF | GA | GD | Pts |
|---|---|---|---|---|---|---|---|---|
| Trinidad and Tobago | 3 | 3 | 0 | 0 | 11 | 2 | +9 | 9 |
 Jamaica | 3 | 2 | 0 | 1 | 7 | 3 | +4 | 6 |
| Grenada | 3 | 1 | 0 | 2 | 3 | 10 | −7 | 3 |
| Guadeloupe | 3 | 0 | 0 | 3 | 4 | 10 | −6 | 0 |
| Jamaica | 5–1 | Guadeloupe |
|---|---|---|
| Davis 43' Griffiths 57'Graham 62', 74', 83' | Plumasseau Didier 69' |
| Team | Pld | W | D | L | GF | GA | GD | Pts |
|---|---|---|---|---|---|---|---|---|
| Cuba | 3 | 3 | 0 | 0 | 6 | 1 | +5 | 9 |
| Haiti | 3 | 2 | 0 | 1 | 7 | 6 | +1 | 6 |
 Brazil U-20 | 3 | 1 | 0 | 2 | 8 | 5 | +3 | 3 |
| Saint Kitts and Nevis | 3 | 0 | 0 | 3 | 0 | 9 | −9 | 0 |
| Haiti | 2–0 | Saint Kitts and Nevis |
|---|---|---|
| Vorbe 16' Chevalier |
| Brazil U-20 | 0–1 | Cuba |
|---|---|---|
| Álvarez |
| Brazil U-20 | 3–4 | Haiti |
|---|---|---|
| Tardieu |
| Trinidad and Tobago | 6–1 | Haiti |
|---|---|---|
| Dwarika 19' Eve Andrews 56'Trotman 82'Mason 86'John 89' | Chevalier 53' |
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 | 2–1 (ASDET) | Cuba |
|---|---|---|
| Rougier 66' John  119' | Prado 88' |
| 1999 Caribbean Cup winner |
|---|
 Trinidad and Tobago Seventh title |
Ariel Álvarez (five goals)
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