| Wednesday 18th February 2004 | |||
| 1st Leg | |||
| Antigua and Barbuda | 2-0 | Netherlands Antilles | |
| Haiti | 5-0 | Turks and Caicos Is | (n) |
| US Virgin Islands | 0-4 | St Kitts and Nevis | |
| Saturday 21st February 2004 | |||
| 2nd Leg | |||
| Turks and Caicos Is | 0-2 | Haiti | (n) (0-7) |
| Sunday 22nd February 2004 | |||
| 1st Leg | |||
| British Virgin Is | 0-1 | St Lucia | |
| Cayman Islands | 1-2 | Cuba | |
| Saturday 28th February 2004 | |||
| 1st Leg | |||
| Aruba | 1-2 | Surinam | |
| Grenada | 5-0 | Guyana | |
| Sunday 29th February 2004 | |||
| 1st Leg | |||
| Bermuda | 13-0 | Montserrat | |
| Sunday 14th March 2004 | |||
| 2nd Leg | |||
| Guyana | 1-3 | Grenada | (1-8) |
| Friday 19th March 2004 | |||
| 1st Leg | |||
| Dominican Republic | 0-0 | Anguilla | |
| Sunday 21st March 2004 | |||
| 2nd Leg | |||
| Dominican Republic | 6-0 | Anguilla | (6-0) |
| Montserrat | 0-7 | Bermuda | (0-20) |
| Friday 26th March 2004 | |||
| 1st Leg | |||
| Bahamas | 1-1 | Dominica | |
| Saturday 27th March 2004 | |||
| 2nd Leg | |||
| Cuba | 3-0 | Cayman Islands | (5-1) |
| Surinam | 8-1 | Aruba | (10-2) |
| Sunday 28th March 2004 | |||
| 2nd Leg | |||
| Bahamas | 1-3 | Dominica | (2-4) |
| St Lucia | 9-0 | British Virgin Is | (10-0) |
| Wednesday 31st March 2004 | |||
| 2nd Leg | |||
| Netherlands Antilles | 3-0 | Antigua and Barbuda | (3-2) |
| St Kitts and Nevis | 7-0 | US Virgin Islands | (11-0) |
