← 1999 Caribbean Cup Qualifying →

Feb. 3, 1999 1999 French Guiana 1 - 3 Martinique Martinique 2
Feb. 5, 1999 1999 British Virgin Islands 3 - 1 Montserrat British Virgin Islands 2
Feb. 7, 1999 1999 British Virgin Islands 3 - 0 Montserrat British Virgin Islands 2
Feb. 24, 1999 1999 Bahamas 3 - 0 Turks and Caicos Islands Bahamas 2
Feb. 26, 1999 1999 Turks and Caicos Islands 2 - 2 U.S. Virgin Islands Bahamas 2
Feb. 28, 1999 1999 Bahamas 0 - 0 U.S. Virgin Islands Bahamas 2
Feb. 28, 1999 1999 Barbados 2 - 2 Guyana Guyana 2
March 6, 1999 1999 Barbados 2 - 0 Guyana Barbados 2
March 10, 1999 1999 Antigua and Barbuda 0 - 2 Barbados Guadeloupe 2
March 10, 1999 1999 Dominica 0 - 1 Guadeloupe Guadeloupe 1
March 12, 1999 1999 Antigua and Barbuda 1 - 2 Guadeloupe Guadeloupe 1
March 12, 1999 1999 Barbados 3 - 1 Dominica Guadeloupe 2
March 14, 1999 1999 Antigua and Barbuda 1 - 1 Dominica Guadeloupe 2
March 14, 1999 1999 Barbados 0 - 1 Guadeloupe Guadeloupe 1
March 17, 1999 1999 British Virgin Islands 0 - 0 Dominican Republic Haiti 2
March 17, 1999 1999 Haiti 2 - 0 Puerto Rico Haiti 2
March 19, 1999 1999 British Virgin Islands 5 - 0 Puerto Rico Haiti 2
March 19, 1999 1999 Dominican Republic 0 - 4 Haiti Haiti 2
March 21, 1999 1999 British Virgin Islands 0 - 6 Haiti Haiti 2
March 21, 1999 1999 Dominican Republic 2 - 0 Puerto Rico Haiti 2
April 17, 1999 1999 Martinique 1 - 3 Saint Lucia Saint Vincent and the Grenadines 2
April 17, 1999 1999 Saint Kitts and Nevis 4 - 3 Saint Vincent and the Grenadines Saint Vincent and the Grenadines 2
April 18, 1999 1999 Martinique 2 - 1 Saint Kitts and Nevis Saint Vincent and the Grenadines 2
April 18, 1999 1999 Saint Lucia 2 - 2 Saint Vincent and the Grenadines Saint Vincent and the Grenadines 2
April 20, 1999 1999 Saint Kitts and Nevis 4 - 3 Saint Lucia Saint Vincent and the Grenadines 2
April 21, 1999 1999 Martinique 1 - 2 Saint Vincent and the Grenadines Saint Vincent and the Grenadines 2
May 4, 1999 1999 Curacao 1 - 3 Grenada Netherlands Antilles 1
May 5, 1999 1999 Bahamas 0 - 6 Bermuda Bermuda 2
May 5, 1999 1999 Cayman Islands 1 - 4 Cuba Bermuda 2
May 6, 1999 1999 Grenada 0 - 0 Suriname Netherlands Antilles 2
May 7, 1999 1999 Bahamas 0 - 7 Cuba Bermuda 2
May 7, 1999 1999 Bermuda 4 - 1 Cayman Islands Bermuda 2
May 8, 1999 1999 Curacao 1 - 1 Suriname Netherlands Antilles 1
May 9, 1999 1999 Bahamas 1 - 4 Cayman Islands Bermuda 2
May 9, 1999 1999 Bermuda 1 - 2 Cuba Bermuda 2