1/16 Finales
| 06/08/2008 | 16:00 | SKA Rostov | 3-2 | Khimki FC |
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| 06/08/2008 | 16:00 | Kamaz Chelni | 1-5 | Tom Tomsk |
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| 06/08/2008 | 16:00 | Alaniya Vladikavkaz | 1-3 | FK Moskou |
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| 06/08/2008 | 16:00 | Salyut Belgorod | 0-1 | Shinnik Yaroslavl |
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| 06/08/2008 | 16:00 | Torpedo Vladimir | 1-4 | CSKA Moskou |
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| 06/08/2008 | 16:00 | Vityaz Podolsk | 2-1 | Spartak Nalchik |
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| 06/08/2008 | 16:00 | Gazovik Orenburg | 2-2P | Kriliya Sovetov |
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| 06/08/2008 | 16:00 | Anzhi Makhachkala | 2-3 | Terek Grozny |
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| 06/08/2008 | 16:00 | Baltika Kaliningrad | 3-0 | Luch Energiya |
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| 06/08/2008 | 16:00 | Sibir Novosibirsk | 1-0 | Zenit St Petersburg |
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| 06/08/2008 | 16:00 | Spartak Nizhniy Novgorod | P1-1 | Saturn Moskou |
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| 06/08/2008 | 16:00 | Metallurg Lipetsk | 0-2 | Lokomotiv Moskou |
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| 06/08/2008 | 16:00 | Dinamo Bryansk | 1-2 | Spartak Moskou |
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| 06/08/2008 | 16:00 | Smeno Komsomolsk | 1-1P | Rubin Kazan |
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| 06/08/2008 | 16:00 | Energiya Khabarovsk | 1-1P | Amkar Perm |
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| 06/08/2008 | 16:00 | Kuban Krasnodar | 0-1 | Dinamo Moskou |
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1/8 Finales
| 23/09/2008 | 17:00 | Dinamo Moskou | 2-0 | SKA Rostov |
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| 24/09/2008 | 13:00 | Tom Tomsk | P2-2 | Spartak Nizhniy Novgorod |
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| 24/09/2008 | 16:00 | Lokomotiv Moskou | 1-0 | Vityaz Podolsk |
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| 24/09/2008 | 16:00 | FK Moskou | 3-0 | Terek Grozny |
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| 24/09/2008 | 16:00 | Kriliya Sovetov | 0-2 | Sibir Novosibirsk |
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| 24/09/2008 | 16:30 | Shinnik Yaroslavl | 1-2 | Spartak Moskou |
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| 24/09/2008 | 17:00 | Rubin Kazan | P0-0 | Amkar Perm |
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| 24/09/2008 | 17:00 | CSKA Moskou | 1-0 | Baltika Kaliningrad |
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Kwart Finales
| 15/04/2009 | 17:00 | Rubin Kazan | 2-0 | Sibir Novosibirsk |
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| 15/04/2009 | 18:00 | Spartak Moskou | 0-3 | Dinamo Moskou |
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| 22/04/2009 | 17:00 | Lokomotiv Moskou | 0-1 | CSKA Moskou |
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| 22/04/2009 | 18:00 | FK Moskou | 2-1 | Tom Tomsk |
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Halve Finales
| 06/05/2009 | 16:30 | FK Moskou | 0-1 | Rubin Kazan |
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| 13/05/2009 | 17:30 | Dinamo Moskou | 2-2P | CSKA Moskou |
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