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Cayman Islands's overall record against each of their opponents during the 1999 season.
| Opposition | P | W | D | L | F | A |
|---|---|---|---|---|---|---|
| Bahamas | 1 | 1 | 0 | 0 | 4 | 1 |
| Bermuda | 1 | 0 | 0 | 1 | 1 | 4 |
| Cuba | 1 | 0 | 0 | 1 | 1 | 4 |
| Haiti | 1 | 0 | 0 | 1 | 0 | 1 |
| Jamaica | 1 | 0 | 0 | 1 | 0 | 4 |
| Netherlands Antilles | 1 | 1 | 0 | 0 | 2 | 0 |