4. Round | 10/04/2009 | Krylia Sovetov | - | FK Khimki | 3:0 | ||||
5. Round | 19/04/2009 | FK Khimki | - | CSKA Moskva | 0:3 | ||||
6. Round | 25/04/2009 | Zenit St. Petersburg | - | FK Khimki | 4:2 | ||||
7. Round | 03/05/2009 | FK Khimki | - | Kuban Krasnodar (1928-2018) | 2:2 | ||||
10. Round | 23/05/2009 | Terek Grozny | - | FK Khimki | 2:0 | ||||
15. Round | 24/07/2009 | FK Khimki | - | FK Amkar Perm | 2:0 | ||||
16. Round | 02/08/2009 | FK Khimki | - | Dinamo Moskva | 0:2 |