| 2. Round | 23/02/2019 | Unión San Felipe | - | Deportes Valdivia | 0:1 | ||||
| 3. Round | 02/03/2019 | Santiago Morning | - | Unión San Felipe | 3:1 | ||||
| 4. Round | 10/03/2019 | Unión San Felipe | - | Santiago Wanderers | 0:1 | ||||
| 5. Round | 17/03/2019 | Santa Cruz | - | Unión San Felipe | 2:0 |  |
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| 7. Round | 07/04/2019 | San Luis | - | Unión San Felipe | 1:1 | ||||
| 14. Round | 26/05/2019 | Deportes Copiapó | - | Unión San Felipe | 0:1 | ||||
| 17. Round | 04/08/2019 | Santiago Wanderers | - | Unión San Felipe | 1:2 | ||||
| 18. Round | 10/08/2019 | Unión San Felipe | - | Rangers | 4:0 |  |
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| 19. Round | 17/08/2019 | CD Magallanes | - | Unión San Felipe | 0:1 | |
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| 20. Round | 25/08/2019 | Cobreloa | - | Unión San Felipe | 1:0 | ||||
| 21. Round | 31/08/2019 | Unión San Felipe | - | Puerto Montt | 2:1 |  |
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| 22. Round | 08/09/2019 | Ñublense | - | Unión San Felipe | 3:1 | |
Chile