| 1. Round | 20/07/2008 | Zorya Lugansk | - | Metalist Kharkiv | 1:1 | ||||
| 2. Round | 30/07/2008 | Metalist Kharkiv | - | Tavriya Simferopol (1958-2014) | 3:0 | ||||
| 3. Round | 02/08/2008 | Dinamo Kiev | - | Metalist Kharkiv | 1:2 | ||||
| 4. Round | 10/08/2008 | Metalist Kharkiv | - | FK Lviv | 0:0 | ||||
| 6. Round | 22/08/2008 | Metalist Kharkiv | - | FK Illichivets | 2:0 | ||||
| 7. Round | 01/09/2008 | Dnipro Dnipropetrovsk | - | Metalist Kharkiv | 2:0 |  |
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| 8. Round | 21/09/2008 | Karpaty Lviv | - | Metalist Kharkiv | 0:2 | ||||
| 9. Round | 27/09/2008 | Metalist Kharkiv | - | Vorskla Poltava | 3:1 | ||||
| 10. Round | 05/10/2008 | Metalurg Zaporizhya | - | Metalist Kharkiv | 1:0 | ||||
| 11. Round | 18/10/2008 | Metalist Kharkiv | - | Arsenal Kiev | 3:1 |  |
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| 14. Round | 09/11/2008 | FK Krivbas (old) | - | Metalist Kharkiv | 1:3 |  |
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| 15. Round | 16/11/2008 | Metalist Kharkiv | - | FK Kharkiv | 1:1 | ||||
| 16. Round | 21/11/2008 | Metalist Kharkiv | - | Zorya Lugansk | 2:1 | |
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| 17. Round | 30/11/2008 | Tavriya Simferopol (1958-2014) | - | Metalist Kharkiv | 0:1 | |
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Ukraine