| 1. Round | 04/01/2014 | Santiago Wanderers | - | Huachipato | 4:2 | ||||
| 2. Round | 09/01/2014 | Audax Italiano | - | Santiago Wanderers | 2:0 | ||||
| 3. Round | 13/01/2014 | Santiago Wanderers | - | Palestino | 2:2 | ||||
| 4. Round | 27/01/2014 | Santiago Wanderers | - | Cobreloa | 2:2 | ||||
| 5. Round | 01/02/2014 | O'Higgins | - | Santiago Wanderers | 2:0 |  |
|||
| 15. Round | 13/04/2014 | Colo-Colo | - | Santiago Wanderers | 1:0 |
Chile