| 2. Round | 15/06/2008 | Trinidad & Tobago | - | Bermuda | 1:2 | ||||
| 2. Round | 22/06/2008 | Bermuda | - | Trinidad & Tobago | 0:2 |  |
|||
| Semi-finals Group A | 21/08/2008 | Cuba | - | Trinidad & Tobago | 1:3 | |
|||
| Semi-finals Group A | 11/09/2008 | USA | - | Trinidad & Tobago | 3:0 | ||||
| Semi-finals Group A | 16/10/2008 | Trinidad & Tobago | - | USA | 2:1 | ||||
| Final round | 12/02/2009 | El Salvador | - | Trinidad & Tobago | 2:2 | ||||
| Final round | 02/04/2009 | USA | - | Trinidad & Tobago | 3:0 | ||||
| Final round | 11/06/2009 | Mexico | - | Trinidad & Tobago | 2:1 |
Trinidad & Tobago