| 5. Round | 17/08/2014 | Universidad Católica | - | Santiago Wanderers | 0:1 | ||||
| 6. Round | 23/08/2014 | Santiago Wanderers | - | Audax Italiano | 2:2 |  |
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| 9. Round | 27/09/2014 | Universidad de Concepción | - | Santiago Wanderers | 1:3 | ||||
| 10. Round | 12/10/2014 | Santiago Wanderers | - | Unión Española | 1:0 |  |
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| 11. Round | 18/10/2014 | Palestino | - | Santiago Wanderers | 0:1 | ||||
| 12. Round | 25/10/2014 | Santiago Wanderers | - | San Marcos | 2:1 | |
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| 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