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| 1st(1st leg) | Aruba | - | Barbados | 1:3 | ||
| 2nd (2nd leg) | Barbados | - | Aruba | 4:0 | ||
| 1st(1st leg): 01/04/2000 | 2nd (2nd leg): 16/04/2000 | Winner: Barbados | ||||
| 1st(1st leg) | Haiti | - | Bahamas | 9:0 | ||
| 2nd (2nd leg) | Bahamas | - | Haiti | 0:4 | ||
| 1st(1st leg): 01/04/2000 | 2nd (2nd leg): 16/04/2000 | Winner: Haiti | ||||
| 1st(1st leg) | Cuba | - | Suriname | 1:0 | ||
| 2nd (2nd leg) | Suriname | - | Cuba | 0:0 | ||
| 1st(1st leg): 02/04/2000 | 2nd (2nd leg): 16/04/2000 | Winner: Cuba | ||||
| 1st(1st leg) | Trinidad & Tobago | - | Dom. Republic | 3:0 | ||
| 2nd (2nd leg) | Dom. Republic | - | Trinidad & Tobago | 0:1 | ||
| 1st(1st leg): 02/04/2000 | 2nd (2nd leg): 16/04/2000 | Winner: Trinidad & Tobago | ||||
| 1st(1st leg) | St. Vincent/Grenadines | - | St. Kitts & Nevis | 1:0 | ||
| 2nd (2nd leg) | St. Kitts & Nevis | - | St. Vincent/Grenadines | 1:2 | ||
| 1st(1st leg): 16/04/2000 | 2nd (2nd leg): 22/04/2000 | Winner: St. Vincent/Grenadines | ||||
| 1st(1st leg) | Antigua & Barbuda | - | Bermuda | 0:0 | ||
| 2nd (2nd leg) | Bermuda | - | Antigua & Barbuda | 1:1 | ||
| 1st(1st leg): 16/04/2000 | 2nd (2nd leg): 23/04/2000 | Winner: Antigua & Barbuda | ||||
