| 1. Round | 08/02/2009 | Bolívar | - | Club San José | 2:1 |  |
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| 2. Round | 15/02/2009 | Real Potosí | - | Club San José | 2:1 | ||||
| 3. Round | 01/03/2009 | Club San José | - | Real Mamoré | 4:2 | |
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| 15. Round | 24/05/2009 | Club San José | - | Club Aurora | 3:0 | ||||
| 19. Round | 14/06/2009 | Universitario de Sucre | - | Club San José | 1:0 | ||||
| 22. Round | 28/06/2009 | Club San José | - | Jorge Wilstermann | 2:1 |
Bolivia