| 16. Round | 30/07/2019 | Deportes Melipilla | - | Santiago Wanderers | 2:1 |  |
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| 17. Round | 04/08/2019 | Santiago Wanderers | - | Unión San Felipe | 1:2 | ||||
| 18. Round | 10/08/2019 | Deportes Temuco | - | Santiago Wanderers | 0:0 | |
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| 19. Round | 17/08/2019 | Santiago Wanderers | - | Puerto Montt | 1:1 | ||||
| 20. Round | 27/08/2019 | Santiago Wanderers | - | Santa Cruz | 3:1 | ||||
| 21. Round | 01/09/2019 | Deportes Valdivia | - | Santiago Wanderers | 0:1 | |
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| 22. Round | 09/09/2019 | Santiago Morning | - | Santiago Wanderers | 2:1 |
Chile