| 1. Round | 04/01/2014 | Santiago Wanderers | - | Huachipato | 4:2 | ||||
| 2. Round | 09/01/2014 | Audax Italiano | - | Santiago Wanderers | 2:0 |  |
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| 3. Round | 13/01/2014 | Santiago Wanderers | - | Palestino | 2:2 | ||||
| 4. Round | 27/01/2014 | Santiago Wanderers | - | Cobreloa | 2:2 | ||||
| 5. Round | 01/02/2014 | O'Higgins | - | Santiago Wanderers | 2:0 | ||||
| 6. Round | 09/02/2014 | Santiago Wanderers | - | Universidad de Chile | 2:1 | ||||
| 7. Round | 16/02/2014 | Deportes Iquique | - | Santiago Wanderers | 3:1 |  |
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| 8. Round | 23/02/2014 | Santiago Wanderers | - | Unión La Calera | 1:0 | ||||
| 9. Round | 02/03/2014 | Everton | - | Santiago Wanderers | 2:1 | |
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| 10. Round | 06/03/2014 | Santiago Wanderers | - | Ñublense | 1:1 | ||||
| 11. Round | 17/03/2014 | Santiago Wanderers | - | Universidad Católica | 0:2 | ||||
| 12. Round | 22/03/2014 | Universidad de Concepción | - | Santiago Wanderers | 2:1 | ||||
| 14. Round | 05/04/2014 | Rangers | - | Santiago Wanderers | 1:0 | ||||
| 15. Round | 13/04/2014 | Colo-Colo | - | Santiago Wanderers | 1:0 | ||||
| 16. Round | 22/04/2014 | Santiago Wanderers | - | Cobresal | 2:0 | ||||
| 17. Round | 26/04/2014 | Antofagasta | - | Santiago Wanderers | 1:1 |
Uruguay