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| 1st(1st leg) | Suriname | - | Jamaica | 0:1 | ||
| 2nd (2nd leg) | Jamaica | - | Suriname | 1:0 | ||
| 1st(1st leg): 31/03/1996 | 2nd (2nd leg): 21/04/1996 | Winner: Jamaica | ||||
| 1st(1st leg) | Puerto Rico | - | St. Vincent/Grenadines | 1:2 | ||
| 2nd (2nd leg) | St. Vincent/Grenadines | - | Puerto Rico | 7:0 | ||
| 1st(1st leg): 04/05/1996 | 2nd (2nd leg): 12/05/1996 | Winner: St. Vincent/Grenadines | ||||
| 1st(1st leg) | Dom. Republic | - | Netherlands Antilles | 2:1 | ||
| 2nd (2nd leg) | Netherlands Antilles | - | Dom. Republic | 0:0 | ||
| 1st(1st leg): 04/05/1996 | 2nd (2nd leg): 11/05/1996 | Winner: Dom. Republic | ||||
| 1st(1st leg) | St. Kitts & Nevis | - | St. Lucia | 5:1 | ||
| 2nd (2nd leg) | St. Lucia | - | St. Kitts & Nevis | 0:1 | ||
| 1st(1st leg): 05/05/1996 | 2nd (2nd leg): 19/05/1996 | Winner: St. Kitts & Nevis | ||||
| 1st(1st leg) | Cayman Islands | - | Cuba | 0:1 | ||
| 2nd (2nd leg) | Cuba | - | Cayman Islands | 5:0 | ||
| 1st(1st leg): 12/05/1996 | 2nd (2nd leg): 14/05/1996 | Winner: Cuba | ||||
| 1st(1st leg) | Haiti | - | Grenada | 6:1 | ||
| 2nd (2nd leg) | Grenada | - | Haiti | 0:1 | ||
| 1st(1st leg): 12/05/1996 | 2nd (2nd leg): 18/05/1996 | Winner: Haiti | ||||
| 1st(1st leg) | Dominica | - | Barbados | 0:1 | ||
| 2nd (2nd leg) | Barbados | - | Dominica | 1:0 | ||
| 1st(1st leg): 14/05/1996 | 2nd (2nd leg): 19/05/1996 | Winner: Barbados | ||||
