| 5. Round | 07/08/2010 | FK Obolon | - | FK Krivbas (old) | 1:1 |  |
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| 6. Round | 14/08/2010 | Metalurg Zaporizhya | - | FK Obolon | 1:2 | ||||
| 7. Round | 20/08/2010 | FK Obolon | - | Zorya Lugansk | 1:0 | ||||
| 8. Round | 28/08/2010 | Arsenal Kiev | - | FK Obolon | 1:0 |  |
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| 10. Round | 19/09/2010 | Karpaty Lviv | - | FK Obolon | 3:0 | |
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| 11. Round | 26/09/2010 | FK Obolon | - | Volyn Lutsk | 0:1 | ||||
| 12. Round | 02/10/2010 | FK Illichivets | - | FK Obolon | 1:0 | |
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| 13. Round | 16/10/2010 | FK Obolon | - | PFK Sevastopol | 2:2 | ||||
| 14. Round | 22/10/2010 | FK Obolon | - | Tavriya Simferopol (1958-2014) | 2:1 | ||||
| 15. Round | 30/10/2010 | Metalist Kharkiv | - | FK Obolon | 2:1 | ||||
| 16. Round | 07/11/2010 | Dinamo Kiev | - | FK Obolon | 0:2 | ||||
| 17. Round | 12/11/2010 | FK Obolon | - | Metalurh Donetsk | 1:1 | |
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| 19. Round | 28/11/2010 | FK Obolon | - | Dnipro Dnipropetrovsk | 0:1 | ||||
| 23. Round | 02/04/2011 | FK Obolon | - | Arsenal Kiev | 1:1 | ||||
| 30. Round | 21/05/2011 | FK Obolon | - | Metalist Kharkiv | 0:2 |
Ukraine