| 18. Round | 27/07/1999 | Torpedo Moskva | - | Krylia Sovetov | 3:1 | ||||
| 19. Round | 03/08/1999 | Krylia Sovetov | - | Lok. Nizhni Novgorod | 3:0 | ||||
| 20. Round | 13/08/1999 | FK Saturn | - | Krylia Sovetov | 2:0 | ||||
| 21. Round | 20/08/1999 | Krylia Sovetov | - | Zhemchuzhina Sochi | 4:2 | ||||
| 22. Round | 28/08/1999 | Lokomotiv Moskva | - | Krylia Sovetov | 2:0 | ||||
| 23. Round | 10/09/1999 | Krylia Sovetov | - | Dinamo Moskva | 1:2 | ||||
| 24. Round | 17/09/1999 | Krylia Sovetov | - | Chernomorets Novorossisk | 1:1 | ||||
| 25. Round | 24/09/1999 | Alania Vladikavkaz | - | Krylia Sovetov | 1:1 | ||||
| 26. Round | 01/10/1999 | Krylia Sovetov | - | Uralan Elista | 0:1 | ||||
| 27. Round | 15/10/1999 | Shinnik Yaroslavl | - | Krylia Sovetov | 1:2 |  |
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| 28. Round | 22/10/1999 | Krylia Sovetov | - | Zenit St. Petersburg | 3:2 | |
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| 30. Round | 07/11/1999 | Krylia Sovetov | - | CSKA Moskva | 1:1 |
Georgia