| 1. Round | 07/08/1999 | Dynamo Dresden | - | Lok Altmark Stendal | 1:1 | ||||
| 2. Round | 15/08/1999 | Lok Altmark Stendal | - | Sachsen Leipzig | 2:3 |  |
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| 3. Round | 22/08/1999 | VFC Plauen | - | Lok Altmark Stendal | 2:1 | ||||
| 4. Round | 25/08/1999 | Lok Altmark Stendal | - | SV Babelsberg 03 | 1:0 | ||||
| 5. Round | 29/08/1999 | Lok Altmark Stendal | - | Erzgebirge Aue | 2:1 | ||||
| 6. Round | 07/09/1999 | FC Carl Zeiss Jena | - | Lok Altmark Stendal | 2:1 | ||||
| 7. Round | 11/09/1999 | Lok Altmark Stendal | - | 1. FC Union Berlin | 1:1 | ||||
| 8. Round | 18/09/1999 | Stahl Eisenhüttenstadt | - | Lok Altmark Stendal | 2:1 | ||||
| 9. Round | 25/09/1999 | Lok Altmark Stendal | - | BFC Dynamo | 5:3 | ||||
| 10. Round | 02/10/1999 | Dresdner SC | - | Lok Altmark Stendal | 2:0 | ||||
| 14. Round | 13/11/1999 | FSV Zwickau | - | Lok Altmark Stendal | 1:1 | ||||
| 15. Round | 20/11/1999 | Lok Altmark Stendal | - | Rot-Weiß Erfurt | 1:1 | ||||
| 16. Round | 05/12/1999 | Hertha BSC II | - | Lok Altmark Stendal | 1:1 |
Germany