| 1. Round | 31/07/1999 | FK Jablonec 97 | - | FC Dukla Pribram | 0:2 |  |
|||
| 2. Round | 08/08/1999 | FC Dukla Pribram | - | Slovan Liberec | 1:1 | ||||
| 3. Round | 15/08/1999 | FK Teplice | - | FC Dukla Pribram | 2:0 |  |
|||
| 6. Round | 11/09/1999 | FC Dukla Pribram | - | Slavia Praha | 1:1 | |
|||
| 7. Round | 19/09/1999 | Dynamo České Budějovice | - | FC Dukla Pribram | 5:0 | ||||
| 8. Round | 24/09/1999 | FC Dukla Pribram | - | Sigma Olomouc | 0:2 | ||||
| 9. Round | 02/10/1999 | FC Boby-sport Brno | - | FC Dukla Pribram | 0:0 | |
|||
| 10. Round | 17/10/1999 | FC Dukla Pribram | - | FC Petra Drnovice | 1:1 | ||||
| 11. Round | 24/10/1999 | CU Bohemians Praha | - | FC Dukla Pribram | 2:0 | ||||
| 12. Round | 31/10/1999 | FC Dukla Pribram | - | Viktoria Žižkov | 5:2 | ||||
| 14. Round | 21/11/1999 | FC Dukla Pribram | - | SFC Opava | 1:0 | ||||
| 15. Round | 28/11/1999 | SK Hradec Králové | - | FC Dukla Pribram | 1:1 | |
Czech Republic