| Group B | 21/08/2009 | San Juan Jabloteh | - | Deportivo Toluca | 0:1 | ||||
| Group B | 27/08/2009 | Marathón | - | San Juan Jabloteh | 3:1 |  |
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| Group B | 16/09/2009 | San Juan Jabloteh | - | D.C. United | 0:1 | ||||
| Group B | 24/09/2009 | Deportivo Toluca | - | San Juan Jabloteh | 3:0 | ||||
| Group B | 01/10/2009 | D.C. United | - | San Juan Jabloteh | 5:1 | ||||
| Group B | 23/10/2009 | San Juan Jabloteh | - | Marathón | 2:4 |
Trinidad & Tobago