 |
 |
|
| 1st(1st leg) | El Nacional | - | Club Nacional | 0:5 (0:0) | ||
| 2nd (2nd leg) | Club Nacional | - | El Nacional | 3:3 (3:3) | ||
| 1st(1st leg): 27/01/2009 | 2nd (2nd leg): 05/02/2009 | Winner: Club Nacional | ||||
| 1st(1st leg) | Universidad de Chile | - | CF Pachuca | 1:0 (1:0) | ||
| 2nd (2nd leg) | CF Pachuca | - | Universidad de Chile | 2:1 (1:0) | ||
| 1st(1st leg): 28/01/2009 | 2nd (2nd leg): 04/02/2009 | Winner: Universidad de Chile | ||||
| 1st(1st leg) | Independiente Medellín | - | Peñarol | 4:0 (3:0) | ||
| 2nd (2nd leg) | Peñarol | - | Independiente Medellín | 0:0 (0:0) | ||
| 1st(1st leg): 28/01/2009 | 2nd (2nd leg): 03/02/2009 | Winner: Independiente Medellín | ||||
| 1st(1st leg) | Palmeiras | - | Real Potosí | 5:1 (3:1) | ||
| 2nd (2nd leg) | Real Potosí | - | Palmeiras | 0:2 (0:1) | ||
| 1st(1st leg): 29/01/2009 | 2nd (2nd leg): 04/02/2009 | Winner: Palmeiras | ||||
| 1st(1st leg) | Sporting Cristal | - | Estudiantes | 2:1 (1:1) | ||
| 2nd (2nd leg) | Estudiantes | - | Sporting Cristal | 1:0 (0:0) | ||
| 1st(1st leg): 29/01/2009 | 2nd (2nd leg): 04/02/2009 | Winner: Estudiantes | ||||
| 1st(1st leg) | Deportivo Anzoátegui | - | Deportivo Cuenca | 2:0 (1:0) | ||
| 2nd (2nd leg) | Deportivo Cuenca | - | Deportivo Anzoátegui | 3:0 (1:0) | ||
| 1st(1st leg): 29/01/2009 | 2nd (2nd leg): 03/02/2009 | Winner: Deportivo Cuenca | ||||
