1. Round | 02/04/1999 | Shinnik Yaroslavl | - | Chernomorets Novorossisk | 1:0 | ||||
2. Round | 10/04/1999 | Chernomorets Novorossisk | - | FK Saturn | 1:1 | ||||
3. Round | 16/04/1999 | Zenit St. Petersburg | - | Chernomorets Novorossisk | 1:1 | ||||
4. Round | 24/04/1999 | Chernomorets Novorossisk | - | Zhemchuzhina Sochi | 3:0 | ||||
5. Round | 01/05/1999 | Spartak Moskva | - | Chernomorets Novorossisk | 2:0 | ||||
6. Round | 08/05/1999 | Chernomorets Novorossisk | - | Lokomotiv Moskva | 1:4 | ||||
7. Round | 14/05/1999 | CSKA Moskva | - | Chernomorets Novorossisk | 5:2 | ||||
8. Round | 21/05/1999 | Chernomorets Novorossisk | - | Dinamo Moskva | 2:1 | ||||
9. Round | 28/05/1999 | Rotor Volgograd (1929-2005) | - | Chernomorets Novorossisk | 5:2 | ||||
10. Round | 12/06/1999 | Chernomorets Novorossisk | - | Krylia Sovetov | 1:1 | ||||
11. Round | 18/06/1999 | Rostselmash Rostov | - | Chernomorets Novorossisk | 1:0 | ||||
12. Round | 22/06/1999 | Chernomorets Novorossisk | - | Alania Vladikavkaz | 1:0 | ||||
13. Round | 26/06/1999 | Torpedo Moskva | - | Chernomorets Novorossisk | 3:1 |