| 2. Round | 15/06/2008 | Trinidad & Tobago | - | Bermuda | 1:2 |  |
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| 2. Round | 22/06/2008 | Bermuda | - | Trinidad & Tobago | 0:2 | |
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| Semi-finals Group A | 16/10/2008 | Trinidad & Tobago | - | USA | 2:1 | ||||
| Semi-finals Group A | 20/11/2008 | Trinidad & Tobago | - | Cuba | 3:0 | ||||
| Final round | 12/02/2009 | El Salvador | - | Trinidad & Tobago | 2:2 | ||||
| Final round | 28/03/2009 | Trinidad & Tobago | - | Honduras | 1:1 | ||||
| Final round | 02/04/2009 | USA | - | Trinidad & Tobago | 3:0 |
Trinidad & Tobago