1/8 Finales
| 28/10/2008 | 16:00 | Obolon Kiev | 1-4 | Vorskla Poltava |
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| 29/10/2008 | 16:00 | Stal Alchivsk | 2-0 | FC Lvov |
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| 29/10/2008 | 16:00 | PFC Olexandria | P1-1 | Dnipro |
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| 29/10/2008 | 16:00 | Dinamo Kiev | 2-0 | Zaria Lugansk |
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| 29/10/2008 | 16:00 | Feniks Illichovets | 0-2 | Tavria Simferopol |
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| 29/10/2008 | 16:00 | Zakarpattia | 1-4 | Shakhtar Donetsk |
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| 29/10/2008 | 16:00 | Metalist Kharkov | 3-1 | Arsenal Kiev |
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| 29/10/2008 | 16:00 | Arsenal Kharkov | 0-2 | Metalurg Donetsk |
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Kwart Finales
| 11/11/2008 | 16:00 | PFC Olexandria | 1-2 | Shakhtar Donetsk |
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| 12/11/2008 | 16:00 | Metalurg Donetsk | 0-1 | Vorskla Poltava |
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| 12/11/2008 | 16:00 | Tavria Simferopol | 1-2 | Metalist Kharkov |
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| 12/11/2008 | 16:00 | Stal Alchivsk | 1-4 | Dinamo Kiev |
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Halve Finales
| 22/04/2009 | 16:00 | Metalist Kharkov | 0-0 | Vorskla Poltava |
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Halve Finales (T)
| 13/05/2009 | 17:00 | Vorskla Poltava | 2-0 | Metalist Kharkov |
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Halve Finales
| 13/05/2009 | 17:45 | Shakhtar Donetsk | 1-0 | Dinamo Kiev |
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Finale
| 31/05/2009 | 16:00 | Vorskla Poltava | 1-0 | Shakhtar Donetsk |
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