| 2. Round | 29/06/2008 | Deportes Melipilla | - | Colo-Colo | 0:2 | ||||
| 3. Round | 06/07/2008 | La Serena | - | Deportes Melipilla | 1:0 | ||||
| 4. Round | 13/07/2008 | Audax Italiano | - | Deportes Melipilla | 2:2 | ||||
| 5. Round | 20/07/2008 | Deportes Melipilla | - | Ñublense | 1:1 | ||||
| 6. Round | 27/07/2008 | Universidad de Chile | - | Deportes Melipilla | 4:1 | ||||
| 7. Round | 03/08/2008 | Deportes Melipilla | - | Provincial Osorno (old) | 3:1 |  |
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| 8. Round | 10/08/2008 | Everton | - | Deportes Melipilla | 2:1 | ||||
| 11. Round | 31/08/2008 | Deportes Melipilla | - | Cobresal | 1:2 |
Argentina