| 1. Jornada | 04.01.2014 | Santiago Wanderers | - | Huachipato | 4:2 |  |
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| 4. Jornada | 28.01.2014 | Santiago Wanderers | - | Cobreloa | 2:2 | ||||
| 5. Jornada | 01.02.2014 | O'Higgins | - | Santiago Wanderers | 2:0 | ||||
| 6. Jornada | 09.02.2014 | Santiago Wanderers | - | Universidad de Chile | 2:1 | ||||
| 7. Jornada | 16.02.2014 | Deportes Iquique | - | Santiago Wanderers | 3:1 | ||||
| 8. Jornada | 23.02.2014 | Santiago Wanderers | - | Unión La Calera | 1:0 | |
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| 9. Jornada | 02.03.2014 | Everton | - | Santiago Wanderers | 2:1 | ||||
| 10. Jornada | 06.03.2014 | Santiago Wanderers | - | Ñublense | 1:1 | ||||
| 11. Jornada | 18.03.2014 | Santiago Wanderers | - | Universidad Católica | 0:2 | ||||
| 12. Jornada | 22.03.2014 | Universidad de Concepción | - | Santiago Wanderers | 2:1 | |
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| 13. Jornada | 29.03.2014 | Santiago Wanderers | - | Unión Española | 4:0 | |
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| 14. Jornada | 05.04.2014 | Rangers | - | Santiago Wanderers | 1:0 |  |
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| 16. Jornada | 22.04.2014 | Santiago Wanderers | - | Cobresal | 2:0 | ||||
| 17. Jornada | 26.04.2014 | Antofagasta | - | Santiago Wanderers | 1:1 | |
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Argentina
