| Sunday 3rd February 2008 | |||
| 1st Leg | |||
| Bermuda | 1-1 | Cayman Islands | |
| Wednesday 6th February 2008 | |||
| 1st Leg | |||
| Aruba | 0-3 | Antigua and Barbuda | |
| Belize | 3-1 | St Kitts and Nevis | (n) |
| Dominica | 1-1 | Barbados | |
| El Salvador | 12-0 | Anguilla | |
| Nicaragua | 0-1 | Netherlands Antilles | |
| Turks and Caicos Is | 2-1 | St Lucia | |
| Wednesday 26th March 2008 | |||
| Grenada | 10-0 | US Virgin Islands | |
| Puerto Rico | 1-0 | Dominican Republic | aet |
| Surinam | 7-1 | Montserrat | (n) |
| 1st Leg | |||
| Bahamas | 1-1 | British Virgin Is | |
| 2nd Leg | |||
| Anguilla | 0-4 | El Salvador | (n) (0-16) |
| Antigua and Barbuda | 1-0 | Aruba | (4-0) |
| Barbados | 1-0 | Dominica | (2-1) |
| Netherlands Antilles | 2-0 | Nicaragua | (3-0) |
| St Kitts and Nevis | 1-1 | Belize | (2-4) |
| St Lucia | 2-0 | Turks and Caicos Is | (3-2) |
| Sunday 30th March 2008 | |||
| 2nd Leg | |||
| Bahamas | 2-2 | British Virgin Is | (3-3) |
| (Bahamas won on away goals) | |||
| Cayman Islands | 1-3 | Bermuda | (2-4) |
