| 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.
Antigua and Barbuda 
Bahamas 
Barbados 
Bermuda 
Brazil U-20 (Invitee)
British Virgin Islands 
Cayman Islands Cuba 
Dominica 
Dominican Republic 
French Guiana (Later withdrew)
Grenada 
Guadeloupe 
Guyana 
Haiti 
Jamaica (Defending Champions)
Martinique 
Montserrat 
Netherlands Antilles 
Puerto Rico 
Saint Lucia 
Saint Kitts and Nevis 
Saint Vincent and the Grenadines 
Suriname Trinidad and Tobago (Hosts)
Turks and Caicos Islands 
U.S. Virgin Islands | 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 |
|---|---|---|
| De Souza 48' Da Silva 70'Salvino 82' | Michel Gabriel 33' Wilson Chevalier 61'Patrick Tardieu 68'De Souza 85' (o.g.) |
| 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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