| 1. Ronde | 04.01.2014 | Santiago Wanderers | - | Huachipato | 4:2 | ||||
| 2. Ronde | 10.01.2014 | Audax Italiano | - | Santiago Wanderers | 2:0 |  |
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| 3. Ronde | 14.01.2014 | Santiago Wanderers | - | Palestino | 2:2 | ||||
| 4. Ronde | 28.01.2014 | Santiago Wanderers | - | Cobreloa | 2:2 | ||||
| 5. Ronde | 01.02.2014 | O'Higgins | - | Santiago Wanderers | 2:0 | ||||
| 6. Ronde | 09.02.2014 | Santiago Wanderers | - | Universidad de Chile | 2:1 | ||||
| 7. Ronde | 16.02.2014 | Deportes Iquique | - | Santiago Wanderers | 3:1 |  |
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| 8. Ronde | 23.02.2014 | Santiago Wanderers | - | Unión La Calera | 1:0 | ||||
| 9. Ronde | 02.03.2014 | Everton | - | Santiago Wanderers | 2:1 | |
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| 10. Ronde | 06.03.2014 | Santiago Wanderers | - | Ñublense | 1:1 | ||||
| 11. Ronde | 18.03.2014 | Santiago Wanderers | - | Universidad Católica | 0:2 | ||||
| 12. Ronde | 22.03.2014 | Universidad de Concepción | - | Santiago Wanderers | 2:1 | ||||
| 14. Ronde | 05.04.2014 | Rangers | - | Santiago Wanderers | 1:0 | ||||
| 15. Ronde | 13.04.2014 | Colo-Colo | - | Santiago Wanderers | 1:0 | ||||
| 16. Ronde | 22.04.2014 | Santiago Wanderers | - | Cobresal | 2:0 | ||||
| 17. Ronde | 26.04.2014 | Antofagasta | - | Santiago Wanderers | 1:1 |
Uruguay