1. Round | 02/04/1999 | CSKA Moskva | - | Krylia Sovetov | 1:1 | ||||
29. Round | 06/04/1999 | Spartak Moskva | - | Krylia Sovetov | 3:0 | ||||
2. Round | 10/04/1999 | Krylia Sovetov | - | Rotor Volgograd (1929-2005) | 0:1 | ||||
5. Round | 01/05/1999 | Lok. Nizhni Novgorod | - | Krylia Sovetov | 3:0 | ||||
6. Round | 08/05/1999 | Krylia Sovetov | - | FK Saturn | 2:0 | ||||
7. Round | 14/05/1999 | Zhemchuzhina Sochi | - | Krylia Sovetov | 0:2 | ||||
8. Round | 21/05/1999 | Krylia Sovetov | - | Lokomotiv Moskva | 1:2 | ||||
9. Round | 28/05/1999 | Dinamo Moskva | - | Krylia Sovetov | 3:3 | ||||
10. Round | 12/06/1999 | Chernomorets Novorossisk | - | Krylia Sovetov | 1:1 | ||||
11. Round | 18/06/1999 | Krylia Sovetov | - | Alania Vladikavkaz | 0:3 | ||||
12. Round | 22/06/1999 | Uralan Elista | - | Krylia Sovetov | 2:1 | ||||
13. Round | 26/06/1999 | Krylia Sovetov | - | Shinnik Yaroslavl | 4:2 | ||||
14. Round | 02/07/1999 | Zenit St. Petersburg | - | Krylia Sovetov | 3:1 |