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| 1st(1st leg) | Trinidad & Tobago | - | Haiti | 3:1 | ||
| 2nd (2nd leg) | Haiti | - | Trinidad & Tobago | 1:1 | ||
| 1st(1st leg): 07/05/2000 | 2nd (2nd leg): 19/05/2000 | Winner: Trinidad & Tobago | ||||
| 1st(1st leg) | Antigua & Barbuda | - | St. Vincent/Grenadines | 2:1 | ||
| 2nd (2nd leg) | St. Vincent/Grenadines | - | Antigua & Barbuda | 4:0 | ||
| 1st(1st leg): 07/05/2000 | 2nd (2nd leg): 21/05/2000 | Winner: St. Vincent/Grenadines | ||||
| 1st(1st leg) | Cuba | - | Barbados | 1:1 | ||
| 2nd (2nd leg) | Barbados | - | Cuba | 5:4 pso | ||
| 1st(1st leg): 07/05/2000 | 2nd (2nd leg): 21/05/2000 | Winner: Barbados | ||||
