| 6. Round | 22/08/2008 | Metalist Kharkiv | - | FK Illichivets | 2:0 | ||||
| 9. Round | 28/09/2008 | FK Illichivets | - | Arsenal Kiev | 2:1 | ||||
| 10. Round | 03/10/2008 | Metalurh Donetsk | - | FK Illichivets | 2:0 | ||||
| 11. Round | 18/10/2008 | FK Illichivets | - | Chernomorets Odessa | 1:0 | ||||
| 12. Round | 25/10/2008 | FK Krivbas (old) | - | FK Illichivets | 0:0 | ||||
| 13. Round | 01/11/2008 | FK Illichivets | - | FK Kharkiv | 1:1 | ||||
| 14. Round | 08/11/2008 | Zorya Lugansk | - | FK Illichivets | 2:1 | ||||
| 15. Round | 15/11/2008 | FK Illichivets | - | Tavriya Simferopol (1958-2014) | 3:3 |  |
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| 17. Round | 29/11/2008 | FK Lviv | - | FK Illichivets | 2:1 | ||||
| 16. Round | 05/12/2008 | FK Illichivets | - | Dinamo Kiev | 3:4 | ||||
| 18. Round | 02/03/2009 | FK Illichivets | - | Shakhtar Donetsk | 1:2 | ||||
| 19. Round | 07/03/2009 | FK Illichivets | - | Karpaty Lviv | 1:5 | ||||
| 20. Round | 14/03/2009 | Dnipro Dnipropetrovsk | - | FK Illichivets | 0:0 | ||||
| 22. Round | 04/04/2009 | Vorskla Poltava | - | FK Illichivets | 2:3 | |
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| 21. Round | 09/04/2009 | FK Illichivets | - | Metalist Kharkiv | 0:2 |
Ukraine