1. Round | 19/07/2009 | FK Obolon | - | Metalist Kharkiv | 0:2 | ||||
2. Round | 26/07/2009 | FK Obolon | - | Zorya Lugansk | 3:0 | ||||
3. Round | 01/08/2009 | Arsenal Kiev | - | FK Obolon | 4:1 | ||||
5. Round | 22/08/2009 | FK Obolon | - | Dnipro Dnipropetrovsk | 1:0 | ||||
6. Round | 30/08/2009 | Karpaty Lviv | - | FK Obolon | 5:0 | ||||
7. Round | 19/09/2009 | FK Obolon | - | Zakarpattya Uzhgorod | 0:1 | ||||
8. Round | 27/09/2009 | Shakhtar Donetsk | - | FK Obolon | 4:0 | ||||
9. Round | 03/10/2009 | FK Obolon | - | Metalurg Zaporizhya | 4:1 | ||||
11. Round | 24/10/2009 | FK Obolon | - | Tavriya Simferopol (1958-2014) | 1:0 | ||||
12. Round | 01/11/2009 | FK Krivbas (old) | - | FK Obolon | 3:2 | ||||
14. Round | 21/11/2009 | Vorskla Poltava | - | FK Obolon | 3:2 | ||||
15. Round | 29/11/2009 | FK Obolon | - | Metalurh Donetsk | 2:1 | ||||
16. Round | 05/12/2009 | Metalist Kharkiv | - | FK Obolon | 0:1 | ||||
17. Round | 12/12/2009 | Zorya Lugansk | - | FK Obolon | 2:0 |