| 1. Round | 06/08/1999 | FSV Zwickau | - | Stahl Eisenhüttenstadt | 4:0 | ||||
| 2. Round | 14/08/1999 | BFC Dynamo | - | FSV Zwickau | 6:1 |  |
|||
| 3. Round | 21/08/1999 | FSV Zwickau | - | Dresdner SC | 0:2 | ||||
| 4. Round | 25/08/1999 | VfB Leipzig | - | FSV Zwickau | 0:0 | ||||
| 5. Round | 28/08/1999 | FSV Zwickau | - | TeBe Berlin II | 1:3 | ||||
| 6. Round | 07/09/1999 | 1. FC Magdeburg | - | FSV Zwickau | 2:2 | |
|||
| 7. Round | 11/09/1999 | SV Babelsberg 03 | - | FSV Zwickau | 0:0 | ||||
| 8. Round | 17/09/1999 | FSV Zwickau | - | Rot-Weiß Erfurt | 1:1 | ||||
| 9. Round | 24/09/1999 | Hertha BSC II | - | FSV Zwickau | 4:1 | ||||
| 10. Round | 02/10/1999 | FSV Zwickau | - | VfL Halle 96 | 0:1 | ||||
| 11. Round | 16/10/1999 | Dynamo Dresden | - | FSV Zwickau | 1:0 |  |
Serbia