7. Round | 11/09/1999 | Lok Altmark Stendal | - | 1. FC Union Berlin | 1:1 | ||||
8. Round | 18/09/1999 | 1. FC Union Berlin | - | Erzgebirge Aue | 1:1 | ||||
9. Round | 25/09/1999 | FC Carl Zeiss Jena | - | 1. FC Union Berlin | 0:1 | ||||
10. Round | 03/10/1999 | 1. FC Union Berlin | - | SV Babelsberg 03 | 4:1 | ||||
11. Round | 16/10/1999 | 1. FC Union Berlin | - | Stahl Eisenhüttenstadt | 3:1 | ||||
12. Round | 23/10/1999 | BFC Dynamo | - | 1. FC Union Berlin | 0:3 | ||||
13. Round | 06/11/1999 | 1. FC Union Berlin | - | Dresdner SC | 1:0 | ||||
14. Round | 13/11/1999 | VfB Leipzig | - | 1. FC Union Berlin | 2:3 | ||||
15. Round | 21/11/1999 | 1. FC Union Berlin | - | TeBe Berlin II | 1:2 | ||||
25. Round | 25/03/2000 | Erzgebirge Aue | - | 1. FC Union Berlin | 2:1 | ||||
27. Round | 11/04/2000 | SV Babelsberg 03 | - | 1. FC Union Berlin | 0:1 | ||||
21. Round | 18/04/2000 | Dynamo Dresden | - | 1. FC Union Berlin | 3:0 | ||||
29. Round | 22/04/2000 | 1. FC Union Berlin | - | BFC Dynamo | 2:1 | ||||
32. Round | 10/05/2000 | TeBe Berlin II | - | 1. FC Union Berlin | 0:2 |