| 19. Round | 07/03/2009 | FK Illichivets | - | Karpaty Lviv | 1:5 | ||||
| 20. Round | 14/03/2009 | Dnipro Dnipropetrovsk | - | FK Illichivets | 0:0 |  |
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| 23. Round | 12/04/2009 | FK Illichivets | - | Metalurg Zaporizhya | 1:1 | ||||
| 24. Round | 17/04/2009 | Arsenal Kiev | - | FK Illichivets | 4:0 | ||||
| 25. Round | 25/04/2009 | FK Illichivets | - | Metalurh Donetsk | 0:1 | ||||
| 26. Round | 02/05/2009 | Chernomorets Odessa | - | FK Illichivets | 3:2 | ||||
| 27. Round | 09/05/2009 | FK Illichivets | - | FK Krivbas (old) | 2:0 | ||||
| 28. Round | 15/05/2009 | FK Kharkiv | - | FK Illichivets | 1:2 | ||||
| 29. Round | 23/05/2009 | FK Illichivets | - | Zorya Lugansk | 1:0 | ||||
| 30. Round | 26/05/2009 | Tavriya Simferopol (1958-2014) | - | FK Illichivets | 3:2 |
Ukraine