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= CFU Caribbean Cup 1999 =
Thu Jun 3
Grenada 2-1 Guadeloupe @ Port of Spain, Trinidad and Tobago
Trinidad and Tobago 1-0 Jamaica @ Port of Spain, Trinidad and Tobago
Fri Jun 4
Cuba 3-1 Haiti @ Macoya, Trinidad and Tobago
Sat Jun 5
Jamaica 5-1 Guadeloupe @ Port of Spain, Trinidad and Tobago
Trinidad and Tobago 7-0 Grenada @ Port of Spain, Trinidad and Tobago
Sun Jun 6
Haiti 2-0 Saint Kitts and Nevis @ Macoya, Trinidad and Tobago
Mon Jun 7
Jamaica 2-1 Grenada @ Port of Spain, Trinidad and Tobago
Trinidad and Tobago 3-2 Guadeloupe @ Port of Spain, Trinidad and Tobago
Tue Jun 8
Cuba 2-0 Saint Kitts and Nevis @ Macoya, Trinidad and Tobago
Thu Jun 10
Cuba 2-0 Jamaica @ Port of Spain, Trinidad and Tobago
Fri Jun 11
Trinidad and Tobago 6-1 Haiti @ Port of Spain, Trinidad and Tobago
Sun Jun 13
Trinidad and Tobago 2-1 Cuba @ Port of Spain, Trinidad and Tobago
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