| 2. Jornada | 26.02.2019 | Santa Cruz | - | Santiago Wanderers | 0:0 | ||||
| 3. Jornada | 02.03.2019 | Puerto Montt | - | Santa Cruz | 0:0 | ||||
| 5. Jornada | 17.03.2019 | Santa Cruz | - | Unión San Felipe | 2:0 | ||||
| 8. Jornada | 13.04.2019 | Santiago Morning | - | Santa Cruz | 1:3 | ||||
| 9. Jornada | 21.04.2019 | Santa Cruz | - | Rangers | 1:1 |  |
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| 13. Jornada | 19.05.2019 | Santa Cruz | - | Deportes Melipilla | 1:0 | ||||
| 16. Jornada | 28.07.2019 | Santa Cruz | - | Ñublense | 1:1 | ||||
| 17. Jornada | 06.08.2019 | Rangers | - | Santa Cruz | 0:3 | ||||
| 18. Jornada | 11.08.2019 | Santa Cruz | - | Santiago Morning | 2:0 | |
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| 19. Jornada | 20.08.2019 | Santa Cruz | - | San Luis | 2:3 | |
Chile