| Wednesday 4th June 2008 | |||
| 1st Leg | |||
| Honduras | 4-0 | Puerto Rico | |
| Saturday 14th June 2008 | |||
| 1st Leg | |||
| Grenada | 2-2 | Costa Rica | |
| Guatemala | 6-0 | St Lucia | |
| Surinam | 1-0 | Guyana | |
| 2nd Leg | |||
| Puerto Rico | 2-2 | Honduras | (2-6) |
| Sunday 15th June 2008 | |||
| 1st Leg | |||
| Belize | 0-2 | Mexico | (n) |
| Haiti | 0-0 | Netherlands Antilles | |
| Jamaica | 7-0 | Bahamas | |
| Panama | 1-0 | El Salvador | |
| St Vincent and Gren | 0-3 | Canada | |
| Trinidad and Tobago | 1-2 | Bermuda | |
| USA | 8-0 | Barbados | |
| Tuesday 17th June 2008 | |||
| 1st Leg | |||
| Antigua and Barbuda | 3-4 | Cuba | |
| Wednesday 18th June 2008 | |||
| 2nd Leg | |||
| Jamaica | 6-0 | Bahamas | (13-0) |
| Friday 20th June 2008 | |||
| 2nd Leg | |||
| Canada | 4-1 | St Vincent and Gren | (7-1) |
| Saturday 21st June 2008 | |||
| 2nd Leg | |||
| Costa Rica | 3-0 | Grenada | (5-2) |
| Mexico | 7-0 | Belize | (9-0) |
| St Lucia | 1-3 | Guatemala | (n) (1-9) |
| Sunday 22nd June 2008 | |||
| 2nd Leg | |||
| Barbados | 0-1 | USA | (0-9) |
| Bermuda | 0-2 | Trinidad and Tobago | (2-3) |
| Cuba | 4-0 | Antigua and Barbuda | (8-3) |
| El Salvador | 3-1 | Panama | (3-2) |
| Guyana | 1-2 | Surinam | (1-3) |
| Netherlands Antilles | 0-1 | Haiti | (0-1) |
