| 1. Round | 27/03/2021 | Curicó Unido | - | Deportes Melipilla | 2:0 | ||||
| 2. Round | 03/04/2021 | Deportes Melipilla | - | Ñublense | 1:1 | ||||
| 3. Round | 10/04/2021 | Unión Española | - | Deportes Melipilla | 0:2 | ||||
| 4. Round | 16/04/2021 | Deportes Melipilla | - | Palestino | 0:1 | ||||
| 5. Round | 27/04/2021 | Audax Italiano | - | Deportes Melipilla | 1:0 | ||||
| 8. Round | 23/05/2021 | Deportes Melipilla | - | Antofagasta | 1:1 | ||||
| 9. Round | 29/05/2021 | La Serena | - | Deportes Melipilla | 5:1 | ||||
| 10. Round | 07/06/2021 | Deportes Melipilla | - | O'Higgins | 3:1 | ||||
| 11. Round | 21/07/2021 | Universidad de Chile | - | Deportes Melipilla | 2:0 | ||||
| 12. Round | 24/07/2021 | Deportes Melipilla | - | Unión La Calera | 3:3 | ||||
| 13. Round | 28/07/2021 | Cobresal | - | Deportes Melipilla | 1:1 | ||||
| 14. Round | 02/08/2021 | Deportes Melipilla | - | Colo-Colo | 2:4 | ||||
| 18. Round | 25/08/2021 | Deportes Melipilla | - | Curicó Unido | 1:1 |
Chile