3. Round | 02/03/2019 | Santiago Wanderers | - | Deportes Temuco | 1:0 | ||||
4. Round | 10/03/2019 | Unión San Felipe | - | Santiago Wanderers | 0:1 | ||||
5. Round | 16/03/2019 | San Luis | - | Santiago Wanderers | 2:2 | ||||
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 | ||||
17. Round | 04/08/2019 | Santiago Wanderers | - | Unión San Felipe | 1:2 | ||||
27. Round | 19/10/2019 | Rangers | - | Santiago Wanderers | 0:1 |