1. Round | 17/02/2019 | Santiago Wanderers | - | Rangers | 0:0 | ||||
2. Round | 25/02/2019 | Santa Cruz | - | Santiago Wanderers | 0:0 | ||||
3. Round | 02/03/2019 | Santiago Wanderers | - | Deportes Temuco | 1:0 | ||||
4. Round | 10/03/2019 | Unión San Felipe | - | Santiago Wanderers | 0:1 | ||||
6. Round | 31/03/2019 | Santiago Wanderers | - | Deportes Valdivia | 2:0 | ||||
7. Round | 07/04/2019 | Ñublense | - | Santiago Wanderers | 0:4 | ||||
8. Round | 14/04/2019 | Santiago Wanderers | - | CD Magallanes | 2:1 | ||||
9. Round | 21/04/2019 | Barnechea | - | Santiago Wanderers | 2:1 | ||||
14. Round | 26/05/2019 | Santiago Wanderers | - | Santiago Morning | 3:1 |