9. Round | 25/09/1999 | FC Carl Zeiss Jena | - | 1. FC Union Berlin | 0:1 | ||||
10. Round | 02/10/1999 | Stahl Eisenhüttenstadt | - | FC Carl Zeiss Jena | 2:1 | ||||
11. Round | 17/10/1999 | FC Carl Zeiss Jena | - | BFC Dynamo | 1:1 | ||||
16. Round | 04/12/1999 | FSV Zwickau | - | FC Carl Zeiss Jena | 0:2 | ||||
17. Round | 10/12/1999 | FC Carl Zeiss Jena | - | Rot-Weiß Erfurt | 1:1 | ||||
18. Round | 05/02/2000 | FC Carl Zeiss Jena | - | Hertha BSC II | 3:1 | ||||
19. Round | 12/02/2000 | VfL Halle 96 | - | FC Carl Zeiss Jena | 0:6 | ||||
20. Round | 19/02/2000 | FC Carl Zeiss Jena | - | Dynamo Dresden | 3:0 |