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| 1st(1st leg) | Trinidad & Tobago | - | Netherlands Antilles | 5:0 (2:0) | ||
| 2nd (2nd leg) | Netherlands Antilles | - | Trinidad & Tobago | 1:1 (1:0) | ||
| 1st(1st leg): 04/03/2000 22:00 | 2nd (2nd leg): 19/03/2000 00:00 | Winner: Trinidad & Tobago | ||||
| 1st(1st leg) | Anguilla | - | Bahamas | 1:3 (0:3) | ||
| 2nd (2nd leg) | Bahamas | - | Anguilla | 2:1 (1:1) | ||
| 1st(1st leg): 05/03/2000 19:00 | 2nd (2nd leg): 19/03/2000 21:00 | Winner: Bahamas | ||||
| 1st(1st leg) | Dom. Republic | - | Montserrat | 3:0 (3:0) | ||
| 2nd (2nd leg) | Montserrat | - | Dom. Republic | 1:3 (0:1) | ||
| 1st(1st leg): 05/03/2000 19:30 | 2nd (2nd leg): 19/03/2000 20:00 | Winner: Dom. Republic | ||||
| 1st(1st leg) | Cuba | - | Cayman Islands | 4:0 (1:0) | ||
| 2nd (2nd leg) | Cayman Islands | - | Cuba | 0:0 (0:0) | ||
| 1st(1st leg): 05/03/2000 20:00 | 2nd (2nd leg): 20/03/2000 00:00 | Winner: Cuba | ||||
| 1st(1st leg) | St. Lucia | - | Suriname | 1:0 (0:0) | ||
| 2nd (2nd leg) | Suriname | - | St. Lucia | 3:1 (0:0, 1:0) pso | ||
| 1st(1st leg): 05/03/2000 20:00 | 2nd (2nd leg): 19/03/2000 21:00 | Winner: Suriname | ||||
| 1st(1st leg) | St. Vincent/Grenadines | - | Virgin Islands | 9:0 (5:0) | ||
| 2nd (2nd leg) | Virgin Islands | - | St. Vincent/Grenadines | 1:5 (0:3) | ||
| 1st(1st leg): 05/03/2000 20:00 | 2nd (2nd leg): 19/03/2000 20:00 | Winner: St. Vincent/Grenadines | ||||
| 1st(1st leg) | Br. Virgin Islands | - | Bermuda | 1:5 (0:2) | ||
| 2nd (2nd leg) | Bermuda | - | Br. Virgin Islands | 9:0 (2:0) | ||
| 1st(1st leg): 05/03/2000 20:00 | 2nd (2nd leg): 19/03/2000 19:00 | Winner: Bermuda | ||||
| 1st(1st leg) | Barbados | - | Grenada | 2:2 (1:1) | ||
| 2nd (2nd leg) | Grenada | - | Barbados | 2:3 (1:2, 2:2) aet | ||
| 1st(1st leg): 05/03/2000 23:00 | 2nd (2nd leg): 18/03/2000 19:30 | Winner: Barbados | ||||
| 1st(1st leg) | Aruba | - | Puerto Rico | 4:2 (0:2) | ||
| 2nd (2nd leg) | Puerto Rico | - | Aruba | 2:2 (2:2) | ||
| 1st(1st leg): 11/03/2000 23:00 | 2nd (2nd leg): 18/03/2000 23:30 | Winner: Aruba | ||||
| 1st(1st leg) | Haiti | - | Dominica | 4:0 (3:0) | ||
| 2nd (2nd leg) | Dominica | - | Haiti | 1:3 (1:0) | ||
| 1st(1st leg): 11/03/2000 23:00 | 2nd (2nd leg): 19/03/2000 20:00 | Winner: Haiti | ||||
| 1st(1st leg) | St. Kitts & Nevis | - | Turks & Caicos | 8:0 (2:0) | ||
| 2nd (2nd leg) | Turks & Caicos | - | St. Kitts & Nevis | 0:6 (0:2) | ||
| 1st(1st leg): 18/03/2000 23:00 | 2nd (2nd leg): 21/03/2000 23:00 | Winner: St. Kitts & Nevis | ||||
