Caribbean Cup 1999 Qualifiers
Preliminary round Group 1
 Bahamas | 4 |
 United States Virgin Islands | 2 |
 Turks and Caicos Islands | 1 |
Preliminary round Group 2
Barbados
Guyana
Preliminary round Group 3
French Guiana
Martinique
Preliminary round Group 4
British Virgin Islands
Montserrat
Qualifying round Group 1
 Cuba | 9 |
 Bermuda | 6 |
 Cayman Islands | 3 |
| Bahamas | 0 |
Qualifying round Group 2
 Guadeloupe | 9 |
| Barbados | 6 |
 Antigua and Barbuda | 1 |
 Dominica | 1 |
Qualifying round Group 3
 Saint Kitts and Nevis | 6 |
 Saint Lucia | 4 |
 Saint Vincent and the Grenadines | 4 |
| Martinique | 3 |
Qualifying round Group 4
 Haiti | 9 |
| British Virgin Islands | 4 |
 Dominican Republic | 4 |
 Puerto Rico | 0 |
Qualifying round Group 5
 Grenada | 4 |
 Suriname | 2 |
 Netherlands Antilles | 1 |
Highlights
Cuba beats Bermuda 2-1 to qualify for 1999 Caribbean Cup
HAMILTON, May. 9, 1999 (AMP) — Trinidad and Tobago 1999 (Qualifiers) : Cuba defeated Bermuda by a score of 2-1 (halftime: 0-0), in a Caribbean Cup qualifying game (Qualifying round Group 1) on Sunday. Cuba secured their ticket to the Caribbean Cup finals.