| 2. Jornada | 15.02.2009 | Real Potosí | - | Club San José | 2:1 | ||||
| 3. Jornada | 01.03.2009 | Club San José | - | Real Mamoré | 4:2 |  |
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| 4. Jornada | 08.03.2009 | Club Aurora | - | Club San José | 4:1 | ||||
| 5. Jornada | 15.03.2009 | Club San José | - | Blooming | 2:1 | ||||
| 6. Jornada | 22.03.2009 | The Strongest | - | Club San José | 2:1 | ||||
| 7. Jornada | 05.04.2009 | Club San José | - | Universitario de Sucre | 3:0 | ||||
| 8. Jornada | 12.04.2009 | Nacional Potosí | - | Club San José | 2:1 | ||||
| 9. Jornada | 18.04.2009 | La Paz FC | - | Club San José | 3:2 | ||||
| 10. Jornada | 26.04.2009 | Jorge Wilstermann | - | Club San José | 0:3 | ||||
| 14. Jornada | 17.05.2009 | Real Mamoré | - | Club San José | 2:3 | ||||
| 16. Jornada | 29.05.2009 | Oriente Petrolero | - | Club San José | 3:1 | ||||
| 18. Jornada | 31.05.2009 | Club San José | - | The Strongest | 5:1 | ||||
| 20. Jornada | 20.06.2009 | Club San José | - | Nacional Potosí | 2:2 |
Paraguay