| 16. Jornada | 30.07.2019 | Deportes Melipilla | - | Santiago Wanderers | 2:1 | ||||
| 17. Jornada | 04.08.2019 | Santiago Wanderers | - | Unión San Felipe | 1:2 | ||||
| 18. Jornada | 10.08.2019 | Deportes Temuco | - | Santiago Wanderers | 0:0 | ||||
| 19. Jornada | 17.08.2019 | Santiago Wanderers | - | Puerto Montt | 1:1 | ||||
| 20. Jornada | 27.08.2019 | Santiago Wanderers | - | Santa Cruz | 3:1 |  |
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| 21. Jornada | 01.09.2019 | Deportes Valdivia | - | Santiago Wanderers | 0:1 | ||||
| 22. Jornada | 09.09.2019 | Santiago Morning | - | Santiago Wanderers | 2:1 | ||||
| 23. Jornada | 15.09.2019 | Santiago Wanderers | - | La Serena | 4:1 | |
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| 24. Jornada | 01.10.2019 | Santiago Wanderers | - | Barnechea | 0:0 | |
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| 25. Jornada | 06.10.2019 | CD Magallanes | - | Santiago Wanderers | 0:2 | ||||
| 26. Jornada | 13.10.2019 | Santiago Wanderers | - | Cobreloa | 5:1 | ||||
| 27. Jornada | 19.10.2019 | Rangers | - | Santiago Wanderers | 0:1 |
Venezuela