1. Round | 02/04/1999 | Zenit St. Petersburg | - | Uralan Elista | 2:0 | ||||
2. Round | 10/04/1999 | Shinnik Yaroslavl | - | Zenit St. Petersburg | 0:0 | ||||
3. Round | 16/04/1999 | Zenit St. Petersburg | - | Chernomorets Novorossisk | 1:1 | ||||
4. Round | 24/04/1999 | Zenit St. Petersburg | - | Spartak Moskva | 1:2 | ||||
5. Round | 01/05/1999 | CSKA Moskva | - | Zenit St. Petersburg | 2:2 | ||||
11. Round | 18/06/1999 | Zhemchuzhina Sochi | - | Zenit St. Petersburg | 1:3 | ||||
12. Round | 22/06/1999 | Zenit St. Petersburg | - | Lokomotiv Moskva | 1:2 | ||||
16. Round | 13/07/1999 | Zenit St. Petersburg | - | Shinnik Yaroslavl | 2:1 | ||||
17. Round | 20/07/1999 | Chernomorets Novorossisk | - | Zenit St. Petersburg | 1:0 | ||||
21. Round | 20/08/1999 | Zenit St. Petersburg | - | Rostselmash Rostov | 1:0 | ||||
24. Round | 17/09/1999 | FK Saturn | - | Zenit St. Petersburg | 1:0 | ||||
25. Round | 24/09/1999 | Zenit St. Petersburg | - | Zhemchuzhina Sochi | 3:1 | ||||
26. Round | 01/10/1999 | Lokomotiv Moskva | - | Zenit St. Petersburg | 1:1 | ||||
27. Round | 15/10/1999 | Zenit St. Petersburg | - | Dinamo Moskva | 0:0 | ||||
28. Round | 22/10/1999 | Krylia Sovetov | - | Zenit St. Petersburg | 3:2 |