The Caribbean Cup, established in 1989, was the championship tournament for national association football teams that are members of the Caribbean Football Union.

Entrants

Withdraws

Qualifying tournament

Preliminary round

Group A

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
Source: [citation needed]
Bahamas 3–0 Turks and Caicos Islands
U.S. Virgin Islands 2–2 Turks and Caicos Islands
Bryan
Bahamas 0–0 U.S. Virgin Islands

Group B

Guyana 2–2 Barbados
Barbados 2–0 Guyana

Group C

Martinique 3–1 French Guiana
French Guiana n / p Martinique

French Guiana withdrew

Group D

 Anguilla withdrew, leaving British Virgin Islands and Montserrat to compete.

British Virgin Islands 3–1 Montserrat
Webb
British Virgin Islands 3–0 Montserrat

Group E

 Aruba and  Sint Maarten both withdrew.

Qualifying round

Group 1

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
Source: [citation needed]
Cayman Islands 1–4 Cuba
Anderson Darcourt
Bobadilla
Roldán
Bermuda 6–0 Bahamas
Lightbourne
Wade
Robinson
Bermuda 4–1 Cayman Islands
Smith
Boyles 		Brown
Cuba 7–0 Bahamas
Bermuda 1–2 Cuba
Smith
Cayman Islands 4 - 1 Bahamas
Whittaker
Brown
Dinnall

Group 2

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
Source: [citation needed]
Barbados 2–0 Antigua and Barbuda
Guadeloupe 1–0 Dominica
Barbados 3–1 Dominica
Guadeloupe 2–1 Antigua and Barbuda
Antigua and Barbuda 1–1 Dominica
Guadeloupe 1–0 Barbados

Group 3

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
Source: [citation needed]
Saint Lucia 3–1 Martinique
Saint Vincent and the Grenadines 3–4 Saint Kitts and Nevis
Saint Kitts and Nevis 1–2 Martinique
Saint Vincent and the Grenadines 2–2 Saint Lucia
Saint Kitts and Nevis 4–3 Saint Lucia
Saint Vincent and the Grenadines 2–1 Martinique

Group 4

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
Source: [citation needed]
Dominican Republic 0–0 British Virgin Islands
Haiti 2–0 Puerto Rico
Haiti 4–0 Dominican Republic
Puerto Rico 0–5 British Virgin Islands
Dominican Republic 2–0 Puerto Rico
Haiti 6–0 British Virgin Islands

Group 5

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
Source: [citation needed]
Netherlands Antilles 1–3 Grenada
Grenada 0–0 Suriname
Netherlands Antilles 1–1 Suriname

Final tournament

Group 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
Source: [citation needed]
Grenada 2–1 Guadeloupe
Roberts
Trinidad and Tobago 1–0 Jamaica
John
Jamaica 5–1 Guadeloupe
Davis 43'
Griffiths 57'
Graham 62', 74', 83'		 Plumasseau Didier 69'
Trinidad and Tobago 7–0 Grenada
Prosper 5', 9', 41'
Eve 28'
Dwarika 35'
Trotman 48', ?'
Jamaica 2–1 Grenada
Graham 62'
Fuller 72'		 Roberts 32'
Trinidad and Tobago 3–2 Guadeloupe
Prosper
Mason 84', 90'		 Damas-Agis

Group 2

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
Source: [citation needed]
Cuba 3–1 Haiti
Martén 28', 50'
Álvarez 40'		 Tardieu 12'
Brazil U-20 5–0 Saint Kitts and Nevis
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.)
Cuba 2–0 Saint Kitts and Nevis
Álvarez 36', 87'

Semi-finals

Cuba 2–0 Jamaica
Gandara 55' (pen.)
Álvarez 89'
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.

Third-place match

Jamaica v Haiti

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 gold-colored soccer ball 119'		 Prado 88'
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

Cuba Raciel Martinez

  • Top Goalscorer

Cuba Ariel Álvarez (five goals)

  • Top Goalkeeper

Trinidad and Tobago Clayton Ince

  • Fair Play Trophy:

 Jamaica

Top goalscorers

Five goals
Four goals
Three goals
Two goals
Allikas: http://en.wikipedia.org/wiki/1999_Caribbean_Cup
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