| 2. Round | 16/06/2008 | Jamaica | - | Bahamas | 7:0 |  |
|||
| 2. Round | 18/06/2008 | Bahamas | - | Jamaica | 0:6 | |
|||
| Semi-finals Group B | 21/08/2008 | Canada | - | Jamaica | 1:1 | ||||
| Semi-finals Group B | 11/09/2008 | Honduras | - | Jamaica | 2:0 | ||||
| Semi-finals Group B | 12/10/2008 | Jamaica | - | Mexico | 1:0 | ||||
| Semi-finals Group B | 16/10/2008 | Jamaica | - | Honduras | 1:0 | |
|||
| Semi-finals Group B | 20/11/2008 | Jamaica | - | Canada | 3:0 | |
Jamaica