| 1. Jornada | 16.01.2016 | San Marcos | - | Santiago Wanderers | 0:2 | ||||
| 2. Jornada | 22.01.2016 | Santiago Wanderers | - | San Luis | 3:1 |  |
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| 3. Jornada | 31.01.2016 | Universidad Católica | - | Santiago Wanderers | 4:2 | |
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| 4. Jornada | 05.02.2016 | Santiago Wanderers | - | O'Higgins | 3:1 | ||||
| 5. Jornada | 14.02.2016 | Huachipato | - | Santiago Wanderers | 3:2 | |
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| 6. Jornada | 19.02.2016 | Santiago Wanderers | - | Palestino | 0:0 | |
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| 7. Jornada | 29.02.2016 | Unión La Calera | - | Santiago Wanderers | 3:3 | ||||
| 8. Jornada | 06.03.2016 | Santiago Wanderers | - | Cobresal | 3:1 | ||||
| 9. Jornada | 12.03.2016 | Deportes Iquique | - | Santiago Wanderers | 1:2 | ||||
| 10. Jornada | 02.04.2016 | Santiago Wanderers | - | Universidad de Chile | 5:4 | ||||
| 13. Jornada | 17.04.2016 | Unión Española | - | Santiago Wanderers | 2:2 | ||||
| 14. Jornada | 24.04.2016 | Santiago Wanderers | - | Antofagasta | 1:1 |  |
Argentina