14. Round | 26/05/2019 | Santiago Wanderers | - | Santiago Morning | 3:1 | ||||
21. Round | 01/09/2019 | Deportes Valdivia | - | Santiago Wanderers | 0:1 | ||||
23. Round | 15/09/2019 | Santiago Wanderers | - | La Serena | 4:1 | ||||
25. Round | 06/10/2019 | CD Magallanes | - | Santiago Wanderers | 0:2 | ||||
26. Round | 13/10/2019 | Santiago Wanderers | - | Cobreloa | 5:1 | ||||
27. Round | 19/10/2019 | Rangers | - | Santiago Wanderers | 0:1 |