| 16. Round | 04/12/1999 | Dynamo Dresden | - | Sachsen Leipzig | 0:1 | ||||
| 17. Round | 11/12/1999 | VFC Plauen | - | Dynamo Dresden | 1:1 |  |
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| 18. Round | 06/02/2000 | Lok Altmark Stendal | - | Dynamo Dresden | 1:1 | ||||
| 19. Round | 12/02/2000 | Dynamo Dresden | - | Erzgebirge Aue | 1:1 | ||||
| 20. Round | 19/02/2000 | FC Carl Zeiss Jena | - | Dynamo Dresden | 3:0 |  |
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| 22. Round | 04/03/2000 | Stahl Eisenhüttenstadt | - | Dynamo Dresden | 4:1 | |
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| 24. Round | 18/03/2000 | Dresdner SC | - | Dynamo Dresden | 2:2 |  |
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| 21. Round | 18/04/2000 | Dynamo Dresden | - | 1. FC Union Berlin | 3:0 | ||||
| 29. Round | 22/04/2000 | Dynamo Dresden | - | Rot-Weiß Erfurt | 2:0 | |
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| 23. Round | 26/04/2000 | Dynamo Dresden | - | BFC Dynamo | 1:1 | |
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| 30. Round | 30/04/2000 | Hertha BSC II | - | Dynamo Dresden | 1:1 | ||||
| 31. Round | 06/05/2000 | Dynamo Dresden | - | VfL Halle 96 | 3:1 | |
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| 32. Round | 10/05/2000 | SV Babelsberg 03 | - | Dynamo Dresden | 1:0 | ||||
| 33. Round | 13/05/2000 | Sachsen Leipzig | - | Dynamo Dresden | 0:0 | ||||
| 34. Round | 20/05/2000 | Dynamo Dresden | - | VFC Plauen | 1:0 |
Serbia