| 1. Round | 01/08/1998 | SV Babelsberg 03 | - | Chemnitzer FC | 0:2 | ||||
| 2. Round | 09/08/1998 | Chemnitzer FC | - | VfB Leipzig | 4:3 | ||||
| 3. Round | 15/08/1998 | VFC Plauen | - | Chemnitzer FC | 0:0 |  |
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| 4. Round | 19/08/1998 | Chemnitzer FC | - | Dresdner SC | 3:0 | ||||
| 5. Round | 23/08/1998 | Lok Altmark Stendal | - | Chemnitzer FC | 0:0 | ||||
| 6. Round | 02/09/1998 | Chemnitzer FC | - | Rot-Weiß Erfurt | 1:1 | ||||
| 7. Round | 13/09/1998 | Erzgebirge Aue | - | Chemnitzer FC | 1:0 | ||||
| 8. Round | 19/09/1998 | Chemnitzer FC | - | Spandauer SV | 2:1 | ||||
| 9. Round | 26/09/1998 | Stahl Eisenhüttenstadt | - | Chemnitzer FC | 0:0 | ||||
| 11. Round | 16/10/1998 | Dynamo Dresden | - | Chemnitzer FC | 2:1 | ||||
| 12. Round | 24/10/1998 | Chemnitzer FC | - | FC Berlin | 1:1 | ||||
| 18. Round | 23/01/1999 | Chemnitzer FC | - | SV Babelsberg 03 | 4:0 | ||||
| 19. Round | 29/01/1999 | VfB Leipzig | - | Chemnitzer FC | 2:0 | |
Croatia