1999 Caribbean Cup
| 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 |
← 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.
Qualifying Tournament
Preliminary round
Group A
| Team | Pts | Pld | W | D | L | GF | GA |
|---|---|---|---|---|---|---|---|
 Bahamas
|
4 | 2 | 1 | 1 | 0 | 3 | 0 |
 U.S. Virgin Islands
|
2 | 2 | 0 | 2 | 0 | 2 | 2 |
 Turks and Caicos Islands
|
1 | 2 | 0 | 1 | 1 | 2 | 5 |
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 | Pts | Pld | W | D | L | GF | GA |
|---|---|---|---|---|---|---|---|
| Cuba
|
9 | 3 | 3 | 0 | 0 | 13 | 2 |
 Bermuda
|
6 | 3 | 2 | 0 | 1 | 11 | 3 |
 Cayman Islands
|
3 | 3 | 1 | 0 | 2 | 6 | 9 |
| Bahamas
|
0 | 3 | 0 | 0 | 3 | 1 | 17 |
| Bermuda | 4–1 | Cayman Islands |
|---|---|---|
Smith  Boyles |
Brown |
| Cayman Islands | 4 - 1 | Bahamas |
|---|---|---|
| Whittaker Brown Dinnall |
Group 2
| Team | Pts | Pld | W | D | L | GF | GA |
|---|---|---|---|---|---|---|---|
 Guadeloupe
|
9 | 3 | 3 | 0 | 0 | 4 | 1 |
 Barbados
|
6 | 3 | 2 | 0 | 1 | 5 | 2 |
 Antigua and Barbuda
|
1 | 3 | 0 | 1 | 2 | 2 | 5 |
 Dominica
|
1 | 3 | 0 | 1 | 2 | 2 | 5 |
Group 3
| Team | Pts | Pld | W | D | L | GF | GA |
|---|---|---|---|---|---|---|---|
 Saint Kitts and Nevis
|
6 | 3 | 2 | 0 | 1 | 9 | 8 |
 Saint Lucia
|
4 | 3 | 1 | 1 | 1 | 8 | 7 |
 Saint Vincent and the Grenadines
|
4 | 3 | 1 | 1 | 1 | 7 | 7 |
 Martinique
|
3 | 3 | 1 | 0 | 2 | 4 | 6 |
Group 4
| Team | Pts | Pld | W | D | L | GF | GA |
|---|---|---|---|---|---|---|---|
 Haiti
|
9 | 3 | 3 | 0 | 0 | 12 | 0 |
 British Virgin Islands
|
4 | 3 | 1 | 1 | 1 | 5 | 6 |
 Dominican Republic
|
4 | 3 | 1 | 1 | 1 | 2 | 4 |
 Puerto Rico
|
0 | 3 | 0 | 0 | 3 | 0 | 9 |
| Haiti | 2–0 | Puerto Rico |
|---|---|---|
Group 5
Saint-Martin withdrew
| Team | Pts | Pld | W | D | L | GF | GA |
|---|---|---|---|---|---|---|---|
 Grenada
|
4 | 2 | 1 | 1 | 0 | 3 | 1 |
 Suriname
|
2 | 2 | 0 | 2 | 0 | 1 | 1 |
 Netherlands Antilles
|
1 | 2 | 0 | 1 | 1 | 2 | 4 |
Final tournament
Group 1
| Team | Pts | Pld | W | D | L | GF | GA |
|---|---|---|---|---|---|---|---|
| Trinidad and Tobago
|
9 | 3 | 3 | 0 | 0 | 11 | 2 |
 Jamaica
|
6 | 3 | 2 | 0 | 1 | 7 | 3 |
| Grenada
|
3 | 3 | 1 | 0 | 2 | 3 | 10 |
| Guadeloupe
|
0 | 3 | 0 | 0 | 3 | 4 | 10 |
| Jamaica | 5–1 | Guadeloupe |
|---|---|---|
| Davis 43' Griffiths 57'Graham 62', 74', 83' |
Plumasseau Didier 69' |
| Trinidad and Tobago | 3–2 | Guadeloupe |
|---|---|---|
| Prosper Mason 84', 90' |
Damas-Agis |
Group 2
| Team | Pts | Pld | W | D | L | GF | GA |
|---|---|---|---|---|---|---|---|
| Cuba
|
9 | 3 | 3 | 0 | 0 | 6 | 1 |
| Haiti
|
6 | 3 | 2 | 0 | 1 | 7 | 6 |
 Brazil
|
3 | 3 | 1 | 0 | 2 | 8 | 5 |
| Saint Kitts and Nevis
|
0 | 3 | 0 | 0 | 3 | 0 | 9 |
| Haiti | 2–0 | Saint Kitts and Nevis |
|---|---|---|
| Vorbe 16' Chevalier |
| Cuba | 2–0 | Saint Kitts and Nevis |
|---|---|---|
| Álvarez 36', 87' |
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) | Cuba |
|---|---|---|
| Rougier 66' John  119' |
Prado 88' |
Result
| 1999 Caribbean Cup Winner |
|---|
 Trinidad and Tobago Seventh title |
Awards
- Most Valuable Player
- Top Goalscorer
Ariel Álvarez (five goals)
- Top Goalkeeper
- Fair Play Trophy:
Top goalscorers
|
|