| 2. Round | 08/06/2019 | Deportes Melipilla | - | Unión Española | 0:0 | ||||
| 2. Round | 11/07/2019 | Unión Española | - | Deportes Melipilla | 4:3 pso |  |
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| Round of 16 | 13/07/2019 | Unión Española | - | Deportes Valdivia | 0:0 | ||||
| Round of 16 | 05/09/2019 | Deportes Valdivia | - | Unión Española | 0:2 | ||||
| Quarter-finals | 08/09/2019 | Audax Italiano | - | Unión Española | 0:1 | ||||
| Quarter-finals | 12/10/2019 | Unión Española | - | Audax Italiano | 2:1 |
Chile