Bolívar 2-1 The Strongest
| 16.11.2008 | The Strongest | 1-2 | Bolívar | |
| 09.11.2008 | Bolívar | 0-0 | The Strongest | |
Real Mamoré 3-0 CD Guabirá
| 16.11.2008 | CD Guabirá | 0-0 | Real Mamoré | |
| 09.11.2008 | Real Mamoré | 3-0 | CD Guabirá | |
Jorge Wilstermann 3-2 Club Aurora
| 16.11.2008 | Club Aurora | 1-3 | Jorge Wilstermann | |
| 09.11.2008 | Jorge Wilstermann | 0-1 | Club Aurora | |
La Paz FC 4-3 CD San José
| 16.11.2008 | CD San José | 1-3 | La Paz FC | |
| 09.11.2008 | La Paz FC | 1-2 | CD San José | |
*Blooming 5-4 Oriente Petrolero
| 17.11.2008 | Oriente Petrolero | 1-2 | Blooming | |
| 11.11.2008 | Blooming | 3-3 | Oriente Petrolero | |
Real Potosí 6-4 Universitario Sucre
| 16.11.2008 | Universitario Sucre | 2-2 | Real Potosí | |
| 09.11.2008 | Real Potosí | 4-2 | Universitario Sucre | |