1999 Caribbean Cup
| Copa Caribe 1999 | |
|---|---|
| Tournament details | |
| Host country | Trinidad and Tobago | 
| Teams | 27 (from 2 confederations) | 
| Final positions | |
| Champions | |
| Runners-up | |
| Tournament statistics | |
| Top scorer(s) | (5 goals)  | 
| Best player(s) | |
← 1998  2001 →   | |
The Caribbean Cup, established in 1989, was the championship tournament for national association football teams that are members of the Caribbean Football Union.
Entrants
 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
Withdraws
Qualifying tournament
Preliminary round
Group A
| Team | Pld | W | D | L | GF | GA | GD | Pts | 
|---|---|---|---|---|---|---|---|---|
| 2 | 1 | 1 | 0 | 3 | 0 | +3 | 4 | |
| 2 | 0 | 2 | 0 | 2 | 2 | 0 | 2 | |
| 2 | 0 | 1 | 1 | 2 | 5 | −3 | 1 | 
Source: 
Group B
Group C
 French Guiana withdrew
Group D
 Anguilla withdrew, leaving British Virgin Islands and Montserrat to compete.
Group E
 Aruba and 
 Sint Maarten both withdrew.
Qualifying round
Group 1
| Team | Pld | W | D | L | GF | GA | GD | Pts | 
|---|---|---|---|---|---|---|---|---|
| 3 | 3 | 0 | 0 | 13 | 2 | +11 | 9 | |
| 3 | 2 | 0 | 1 | 11 | 3 | +8 | 6 | |
| 3 | 1 | 0 | 2 | 6 | 9 | −3 | 3 | |
| 3 | 0 | 0 | 3 | 1 | 17 | −16 | 0 | 
Source: 
| Cayman Islands  | 1–4 | |
|---|---|---|
| Anderson  | 
Darcourt  Bobadilla Roldán  | 
| Bermuda  | 6–0 | |
|---|---|---|
| Lightbourne  Wade Robinson  | 
| Bermuda  | 4–1 | |
|---|---|---|
| Smith  Boyles  | 
Brown  | 
| Cayman Islands  | 4 - 1 | |
|---|---|---|
| Whittaker  Brown Dinnall  | 
Group 2
| Team | Pld | W | D | L | GF | GA | GD | Pts | 
|---|---|---|---|---|---|---|---|---|
| 3 | 3 | 0 | 0 | 4 | 1 | +3 | 9 | |
| 3 | 2 | 0 | 1 | 5 | 2 | +3 | 6 | |
| 3 | 0 | 1 | 2 | 2 | 5 | −3 | 1 | |
| 3 | 0 | 1 | 2 | 2 | 5 | −3 | 1 | 
Source: 
Group 3
| Team | Pld | W | D | L | GF | GA | GD | Pts | 
|---|---|---|---|---|---|---|---|---|
| 3 | 2 | 0 | 1 | 9 | 8 | +1 | 6 | |
| 3 | 1 | 1 | 1 | 8 | 7 | +1 | 4 | |
| 3 | 1 | 1 | 1 | 7 | 7 | 0 | 4 | |
| 3 | 1 | 0 | 2 | 4 | 6 | −2 | 3 | 
Source: 
Group 4
| Team | Pld | W | D | L | GF | GA | GD | Pts | 
|---|---|---|---|---|---|---|---|---|
| 3 | 3 | 0 | 0 | 12 | 0 | +12 | 9 | |
| 3 | 1 | 1 | 1 | 5 | 6 | −1 | 4 | |
| 3 | 1 | 1 | 1 | 2 | 4 | −2 | 4 | |
| 3 | 0 | 0 | 3 | 0 | 9 | −9 | 0 | 
Source: 
| Haiti  | 2–0 | |
|---|---|---|
Group 5
 Saint-Martin withdrew
| Team | Pld | W | D | L | GF | GA | GD | Pts | 
|---|---|---|---|---|---|---|---|---|
| 2 | 1 | 1 | 0 | 3 | 1 | +2 | 4 | |
| 2 | 0 | 2 | 0 | 1 | 1 | 0 | 2 | |
| 2 | 0 | 1 | 1 | 2 | 4 | −2 | 1 | 
Source: 
Final tournament
Group 1
| Team | Pld | W | D | L | GF | GA | GD | Pts | 
|---|---|---|---|---|---|---|---|---|
| 3 | 3 | 0 | 0 | 11 | 2 | +9 | 9 | |
| 3 | 2 | 0 | 1 | 7 | 3 | +4 | 6 | |
| 3 | 1 | 0 | 2 | 3 | 10 | −7 | 3 | |
| 3 | 0 | 0 | 3 | 4 | 10 | −6 | 0 | 
Source: 
| Jamaica  | 5–1 | |
|---|---|---|
| Davis  Griffiths Graham  | 
Plumasseau Didier  | 
| Trinidad and Tobago  | 3–2 | |
|---|---|---|
| Prosper Mason  | 
Damas-Agis  | 
Group 2
| Team | Pld | W | D | L | GF | GA | GD | Pts | 
|---|---|---|---|---|---|---|---|---|
| 3 | 3 | 0 | 0 | 6 | 1 | +5 | 9 | |
| 3 | 2 | 0 | 1 | 7 | 6 | +1 | 6 | |
| 3 | 1 | 0 | 2 | 8 | 5 | +3 | 3 | |
| 3 | 0 | 0 | 3 | 0 | 9 | −9 | 0 | 
Source: 
| Haiti  | 2–0 | |
|---|---|---|
| Vorbe  Chevalier  | 
| Brazil U-20  | 0–1 | |
|---|---|---|
| Álvarez  | 
| Brazil U-20  | 3–4 | |
|---|---|---|
| De Souza  Da Silva Salvino  | 
Michel Gabriel  Wilson Chevalier Patrick Tardieu De Souza  | 
| Cuba  | 2–0 | |
|---|---|---|
| Álvarez  | 
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
| Trinidad and Tobago  | 2–1 (ASDET) | |
|---|---|---|
| Rougier  John  | 
Prado  | 
Referee: Michael Kennedy
Result
| 1999 Caribbean Cup winner | 
|---|
Trinidad and Tobago Seventh title  | 
Trinidad and Tobago qualified for the 2000 Gold Cup
Awards
- Most Valuable Player
 
- Top Goalscorer
 
 Ariel Álvarez (five goals)
- Top Goalkeeper
 
- Fair Play Trophy:
 
Top goalscorers
- Five goals
 
- Four goals
 
- Three goals
 
 Wilson Chevalier
 Stern John
 Stokley Mason
- Two goals
 
 Luis Marten
 Damas-Agis Patrice
 Jason Roberts
 Patrick Tardieu
 Mickey Trotman
 Angus Eve
 Arnold Dwarika