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| 1st(1st leg) | D.C. United | - | Luis Ángel Firpo | 1:1 | ||
| 2nd (2nd leg) | Luis Ángel Firpo | - | D.C. United | 4:5 pso | ||
| 1st(1st leg): 29/07/2009 01:00 | 2nd (2nd leg): 05/08/2009 03:05 | Winner: D.C. United | ||||
| 1st(1st leg) | CF Pachuca | - | Deportivo Jalapa | 3:0 | ||
| 2nd (2nd leg) | Deportivo Jalapa | - | CF Pachuca | 1:7 | ||
| 1st(1st leg): 29/07/2009 03:00 | 2nd (2nd leg): 05/08/2009 03:05 | Winner: CF Pachuca | ||||
| 1st(1st leg) | San Francisco FC | - | San Juan Jabloteh | 2:0 | ||
| 2nd (2nd leg) | San Juan Jabloteh | - | San Francisco FC | 3:0 | ||
| 1st(1st leg): 30/07/2009 01:00 | 2nd (2nd leg): 07/08/2009 01:00 | Winner: San Juan Jabloteh | ||||
| 1st(1st leg) | Toronto FC | - | Puerto Rico Islanders | 0:1 | ||
| 2nd (2nd leg) | Puerto Rico Islanders | - | Toronto FC | 0:0 | ||
| 1st(1st leg): 30/07/2009 01:00 | 2nd (2nd leg): 05/08/2009 01:00 | Winner: Puerto Rico Islanders | ||||
| 1st(1st leg) | Municipal Liberia | - | Real España | 3:0 | ||
| 2nd (2nd leg) | Real España | - | Municipal Liberia | 6:0 | ||
| 1st(1st leg): 30/07/2009 03:00 | 2nd (2nd leg): 07/08/2009 03:00 | Winner: Real España | ||||
| 1st(1st leg) | W Connection FC | - | New York RB | 2:2 | ||
| 2nd (2nd leg) | New York RB | - | W Connection FC | 1:2 | ||
| 1st(1st leg): 31/07/2009 01:00 | 2nd (2nd leg): 06/08/2009 01:00 | Winner: W Connection FC | ||||
| 1st(1st leg) | Olimpia | - | Árabe Unido | 2:1 | ||
| 2nd (2nd leg) | Árabe Unido | - | Olimpia | 1:0 | ||
| 1st(1st leg): 31/07/2009 03:00 | 2nd (2nd leg): 07/08/2009 01:00 | Winner: Árabe Unido | ||||
| 1st(1st leg) | CS Herediano | - | Cruz Azul | 2:6 | ||
| 2nd (2nd leg) | Cruz Azul | - | CS Herediano | 0:0 | ||
| 1st(1st leg): 31/07/2009 03:00 | 2nd (2nd leg): 06/08/2009 03:00 | Winner: Cruz Azul | ||||
