| 1. Round | 07/08/1999 | TeBe Berlin II | - | Dresdner SC | 1:4 | ||||
| 4. Round | 24/08/1999 | TeBe Berlin II | - | 1. FC Magdeburg | 1:3 | ||||
| 5. Round | 28/08/1999 | FSV Zwickau | - | TeBe Berlin II | 1:3 |  |
|||
| 6. Round | 07/09/1999 | TeBe Berlin II | - | Rot-Weiß Erfurt | 3:2 | ||||
| 7. Round | 12/09/1999 | Hertha BSC II | - | TeBe Berlin II | 3:2 | |
|||
| 8. Round | 19/09/1999 | TeBe Berlin II | - | VfL Halle 96 | 1:1 | |
|||
| 9. Round | 25/09/1999 | Dynamo Dresden | - | TeBe Berlin II | 1:1 | |
|||
| 10. Round | 01/10/1999 | TeBe Berlin II | - | Sachsen Leipzig | 0:2 | ||||
| 26. Round | 02/04/2000 | TeBe Berlin II | - | Dynamo Dresden | 0:2 | ||||
| 29. Round | 24/04/2000 | Lok Altmark Stendal | - | TeBe Berlin II | 3:0 | ||||
| 30. Round | 28/04/2000 | TeBe Berlin II | - | Erzgebirge Aue | 2:3 | ||||
| 31. Round | 05/05/2000 | FC Carl Zeiss Jena | - | TeBe Berlin II | 2:1 | ||||
| 33. Round | 13/05/2000 | Stahl Eisenhüttenstadt | - | TeBe Berlin II | 2:2 | ||||
| 34. Round | 20/05/2000 | TeBe Berlin II | - | BFC Dynamo | 7:3 |  |
|||
| 28. Round | 12/06/2000 | TeBe Berlin II | - | VFC Plauen | 2:2 |
North Macedonia