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