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Trinidad and Tobago's overall record against each of their opponents during the 1999 season.
| Opposition | P | W | D | L | F | A |
|---|---|---|---|---|---|---|
| Antigua and Barbuda | 1 | 1 | 0 | 0 | 3 | 2 |
| Cuba | 1 | 1 | 0 | 0 | 2 | 1 |
| Dominica | 1 | 1 | 0 | 0 | 8 | 0 |
| Grenada | 1 | 1 | 0 | 0 | 7 | 0 |
| Guadeloupe | 1 | 1 | 0 | 0 | 3 | 2 |
| Haiti | 2 | 2 | 0 | 0 | 10 | 2 |
| Jamaica | 3 | 2 | 0 | 1 | 4 | 2 |
| Martinique | 1 | 1 | 0 | 0 | 2 | 1 |
| South Africa | 1 | 1 | 0 | 0 | 2 | 0 |