| 1. Round | 29/01/2011 | Ñublense | - | Santiago Wanderers | 2:0 | ||||
| 2. Round | 05/02/2011 | Santiago Wanderers | - | Colo-Colo | 2:1 | ||||
| 3. Round | 11/02/2011 | Unión Española | - | Santiago Wanderers | 2:1 | ||||
| 4. Round | 18/02/2011 | Santiago Wanderers | - | Palestino | 1:1 | ||||
| 13. Round | 23/04/2011 | Santiago Wanderers | - | Universidad de Concepción | 2:1 | ||||
| 14. Round | 29/04/2011 | Audax Italiano | - | Santiago Wanderers | 4:0 |  |
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| 15. Round | 07/05/2011 | Santiago Wanderers | - | Cobreloa | 2:0 | ||||
| 16. Round | 14/05/2011 | O'Higgins | - | Santiago Wanderers | 1:1 | ||||
| 17. Round | 22/05/2011 | Santiago Wanderers | - | Unión La Calera | 1:1 |
Chile