| 2. Round | 05/08/2016 | Cobresal | - | Santiago Wanderers | 1:1 | ||||
| 3. Round | 13/08/2016 | Santiago Wanderers | - | Audax Italiano | 2:0 |  |
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| 5. Round | 28/08/2016 | Santiago Wanderers | - | Antofagasta | 0:1 | ||||
| 6. Round | 10/09/2016 | Palestino | - | Santiago Wanderers | 0:0 | ||||
| 7. Round | 24/09/2016 | Colo-Colo | - | Santiago Wanderers | 1:1 | ||||
| 9. Round | 15/10/2016 | Santiago Wanderers | - | Everton | 0:1 | ||||
| 10. Round | 29/10/2016 | Deportes Iquique | - | Santiago Wanderers | 3:0 | ||||
| 11. Round | 05/11/2016 | Santiago Wanderers | - | Unión Española | 0:2 | ||||
| 8. Round | 13/11/2016 | Santiago Wanderers | - | Universidad de Concepción | 2:0 | ||||
| 13. Round | 27/11/2016 | San Luis | - | Santiago Wanderers | 2:1 | ||||
| 14. Round | 01/12/2016 | Santiago Wanderers | - | Huachipato | 0:2 | ||||
| 15. Round | 08/12/2016 | O'Higgins | - | Santiago Wanderers | 4:0 |
Chile