| 1. Jornada | 17.02.2019 | Santiago Wanderers | - | Rangers | 0:0 | ||||
| 2. Jornada | 26.02.2019 | Santa Cruz | - | Santiago Wanderers | 0:0 | ||||
| 3. Jornada | 02.03.2019 | Santiago Wanderers | - | Deportes Temuco | 1:0 | ||||
| 4. Jornada | 10.03.2019 | Unión San Felipe | - | Santiago Wanderers | 0:1 | ||||
| 5. Jornada | 16.03.2019 | San Luis | - | Santiago Wanderers | 2:2 |  |
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| 6. Jornada | 31.03.2019 | Santiago Wanderers | - | Deportes Valdivia | 2:0 | |
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| 7. Jornada | 07.04.2019 | Ñublense | - | Santiago Wanderers | 0:4 | |
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| 8. Jornada | 14.04.2019 | Santiago Wanderers | - | CD Magallanes | 2:1 | ||||
| 9. Jornada | 21.04.2019 | Barnechea | - | Santiago Wanderers | 2:1 | |
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| 10. Jornada | 28.04.2019 | Cobreloa | - | Santiago Wanderers | 4:1 | ||||
| 11. Jornada | 04.05.2019 | Santiago Wanderers | - | Deportes Melipilla | 2:1 | |
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| 12. Jornada | 11.05.2019 | La Serena | - | Santiago Wanderers | 0:0 | ||||
| 13. Jornada | 18.05.2019 | Santiago Wanderers | - | Deportes Copiapó | 0:3 | ||||
| 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 |
Argentina