| 1. Round | 21/06/2008 | Unión Española | - | Deportes Melipilla | 1:0 | ||||
| 3. Round | 06/07/2008 | La Serena | - | Deportes Melipilla | 1:0 | ||||
| 4. Round | 13/07/2008 | Audax Italiano | - | Deportes Melipilla | 2:2 | ||||
| 17. Round | 25/10/2008 | Antofagasta | - | Deportes Melipilla | 4:2 |  |
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| 18. Round | 31/10/2008 | Deportes Melipilla | - | Santiago Morning | 1:5 | ||||
| 19. Round | 08/11/2008 | Universidad de Concepción | - | Deportes Melipilla | 0:1 |
Chile