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| 1st(1st leg) | Dom. Republic | - | Puerto Rico | dnp | ||
| 2nd (2nd leg) | Puerto Rico | - | Dom. Republic | 1:0 (0:0, 0:0) aet | ||
| 1st(1st leg): | 2nd (2nd leg): 27/03/2008 00:00 | Winner: Puerto Rico | ||||
| 1st(1st leg) | Virgin Islands | - | Grenada | dnp | ||
| 2nd (2nd leg) | Grenada | - | Virgin Islands | 10:0 (5:0) | ||
| 1st(1st leg): | 2nd (2nd leg): 26/03/2008 19:00 | Winner: Grenada | ||||
| 1st(1st leg) | Suriname | - | Montserrat | dnp | ||
| 2nd (2nd leg) | Montserrat | - | Suriname | 1:7 (0:2) | ||
| 1st(1st leg): | 2nd (2nd leg): 26/03/2008 22:00 | Winner: Suriname | ||||
| 1st(1st leg) | Bermuda | - | Cayman Islands | 1:1 (1:0) | ||
| 2nd (2nd leg) | Cayman Islands | - | Bermuda | 1:3 (0:2) | ||
| 1st(1st leg): 03/02/2008 19:00 | 2nd (2nd leg): 31/03/2008 00:00 | Winner: Bermuda | ||||
| 1st(1st leg) | Belize | - | St. Kitts & Nevis | 3:1 (3:1) | ||
| 2nd (2nd leg) | St. Kitts & Nevis | - | Belize | 1:1 (0:1) | ||
| 1st(1st leg): 06/02/2008 21:00 | 2nd (2nd leg): 26/03/2008 23:00 | Winner: Belize | ||||
| 1st(1st leg) | Nicaragua | - | Netherlands Antilles | 0:1 (0:1) | ||
| 2nd (2nd leg) | Netherlands Antilles | - | Nicaragua | 2:0 (1:0) | ||
| 1st(1st leg): 06/02/2008 21:00 | 2nd (2nd leg): 27/03/2008 00:00 | Winner: Netherlands Antilles | ||||
| 1st(1st leg) | Dominica | - | Barbados | 1:1 (1:1) | ||
| 2nd (2nd leg) | Barbados | - | Dominica | 1:0 (0:0) | ||
| 1st(1st leg): 06/02/2008 23:00 | 2nd (2nd leg): 26/03/2008 19:00 | Winner: Barbados | ||||
| 1st(1st leg) | Aruba | - | Antigua & Barbuda | 0:3 (0:3) | ||
| 2nd (2nd leg) | Antigua & Barbuda | - | Aruba | 1:0 (0:0) | ||
| 1st(1st leg): 07/02/2008 00:00 | 2nd (2nd leg): 26/03/2008 20:15 | Winner: Antigua & Barbuda | ||||
| 1st(1st leg) | Turks & Caicos | - | St. Lucia | 2:1 (1:0) | ||
| 2nd (2nd leg) | St. Lucia | - | Turks & Caicos | 2:0 (1:0) | ||
| 1st(1st leg): 07/02/2008 00:45 | 2nd (2nd leg): 26/03/2008 19:00 | Winner: St. Lucia | ||||
| 1st(1st leg) | El Salvador | - | Anguilla | 12:0 (4:0) | ||
| 2nd (2nd leg) | Anguilla | - | El Salvador | 0:4 (0:4) | ||
| 1st(1st leg): 07/02/2008 01:30 | 2nd (2nd leg): 27/03/2008 00:00 | Winner: El Salvador | ||||
| 1st(1st leg) | Bahamas | - | Br. Virgin Islands | 1:1 (0:0) | ||
| 2nd (2nd leg) | Br. Virgin Islands | - | Bahamas | 2:2 (0:1) | ||
| 1st(1st leg): 26/03/2008 20:00 | 2nd (2nd leg): 30/03/2008 21:00 | Winner: Bahamas | ||||
