| 1. Round | 19/07/2014 | Santiago Wanderers | - | Barnechea | 3:0 | ||||
| 2. Round | 27/07/2014 | Cobreloa | - | Santiago Wanderers | 1:2 | ||||
| 3. Round | 02/08/2014 | Universidad de Chile | - | Santiago Wanderers | 3:2 | ||||
| 4. Round | 10/08/2014 | Santiago Wanderers | - | Deportes Iquique | 2:0 | ||||
| 5. Round | 17/08/2014 | Universidad Católica | - | Santiago Wanderers | 0:1 |  |
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| 6. Round | 23/08/2014 | Santiago Wanderers | - | Audax Italiano | 2:2 | ||||
| 7. Round | 30/08/2014 | Huachipato | - | Santiago Wanderers | 4:0 | ||||
| 8. Round | 13/09/2014 | Santiago Wanderers | - | Cobresal | 4:1 | ||||
| 9. Round | 27/09/2014 | Universidad de Concepción | - | Santiago Wanderers | 1:3 | |
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| 10. Round | 12/10/2014 | Santiago Wanderers | - | Unión Española | 1:0 | ||||
| 11. Round | 18/10/2014 | Palestino | - | Santiago Wanderers | 0:1 | ||||
| 13. Round | 31/10/2014 | Santiago Wanderers | - | O'Higgins | 1:0 | ||||
| 14. Round | 09/11/2014 | Antofagasta | - | Santiago Wanderers | 0:2 | ||||
| 15. Round | 22/11/2014 | Santiago Wanderers | - | Ñublense | 2:1 | ||||
| 16. Round | 30/11/2014 | Unión La Calera | - | Santiago Wanderers | 0:1 | ||||
| 17. Round | 06/12/2014 | Santiago Wanderers | - | Colo-Colo | 2:0 |
Chile