| 1. Jornada | 04.01.2014 | Santiago Wanderers | - | Huachipato | 4:2 | ||||
| 2. Jornada | 10.01.2014 | Audax Italiano | - | Santiago Wanderers | 2:0 | ||||
| 3. Jornada | 14.01.2014 | Santiago Wanderers | - | Palestino | 2:2 |  |
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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 | ||||
| 10. Jornada | 06.03.2014 | Santiago Wanderers | - | Ñublense | 1:1 | ||||
| 11. Jornada | 18.03.2014 | Santiago Wanderers | - | Universidad Católica | 0:2 | |
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| 12. Jornada | 22.03.2014 | Universidad de Concepción | - | Santiago Wanderers | 2:1 | ||||
| 13. Jornada | 29.03.2014 | Santiago Wanderers | - | Unión Española | 4:0 | ||||
| 14. Jornada | 05.04.2014 | Rangers | - | Santiago Wanderers | 1:0 | |
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| 15. Jornada | 13.04.2014 | Colo-Colo | - | Santiago Wanderers | 1:0 | |
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| 16. Jornada | 22.04.2014 | Santiago Wanderers | - | Cobresal | 2:0 | |
Chile