| 1. Jornada | 01.02.2009 | Santiago Morning | - | Cobreloa | 2:0 | ||||
| 2. Jornada | 08.02.2009 | Audax Italiano | - | Santiago Morning | 1:1 | ||||
| 3. Jornada | 15.02.2009 | Ñublense | - | Santiago Morning | 2:1 | ||||
| 6. Jornada | 01.03.2009 | Santiago Morning | - | Universidad de Concepción | 5:4 | ||||
| 11. Jornada | 28.03.2009 | Santiago Morning | - | Curicó Unido | 0:1 | ||||
| 10. Jornada | 05.04.2009 | Everton | - | Santiago Morning | 1:3 | ||||
| 12. Jornada | 12.04.2009 | Universidad de Chile | - | Santiago Morning | 1:3 | ||||
| 13. Jornada | 19.04.2009 | Santiago Morning | - | Unión Española | 1:3 |  |
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| 14. Jornada | 26.04.2009 | La Serena | - | Santiago Morning | 1:4 | ||||
| 16. Jornada | 09.05.2009 | Santiago Morning | - | Rangers | 2:1 | |
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| 17. Jornada | 17.05.2009 | O'Higgins | - | Santiago Morning | 3:2 |  |
Uruguay