| 1. Ronde | 07.08.1999 | Dynamo Dresden | - | Lok Altmark Stendal | 1:1 |  |
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| 2. Ronde | 15.08.1999 | Lok Altmark Stendal | - | Sachsen Leipzig | 2:3 | |
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| 3. Ronde | 22.08.1999 | VFC Plauen | - | Lok Altmark Stendal | 2:1 | ||||
| 5. Ronde | 29.08.1999 | Lok Altmark Stendal | - | Erzgebirge Aue | 2:1 | ||||
| 6. Ronde | 07.09.1999 | FC Carl Zeiss Jena | - | Lok Altmark Stendal | 2:1 | ||||
| 7. Ronde | 11.09.1999 | Lok Altmark Stendal | - | 1. FC Union Berlin | 1:1 | |
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| 8. Ronde | 18.09.1999 | Stahl Eisenhüttenstadt | - | Lok Altmark Stendal | 2:1 | ||||
| 10. Ronde | 02.10.1999 | Dresdner SC | - | Lok Altmark Stendal | 2:0 | ||||
| 11. Ronde | 17.10.1999 | Lok Altmark Stendal | - | VfB Leipzig | 0:1 | ||||
| 12. Ronde | 24.10.1999 | TeBe Berlin II | - | Lok Altmark Stendal | 0:2 | ||||
| 13. Ronde | 07.11.1999 | Lok Altmark Stendal | - | 1. FC Magdeburg | 1:4 | |
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| 14. Ronde | 13.11.1999 | FSV Zwickau | - | Lok Altmark Stendal | 1:1 | ||||
| 15. Ronde | 20.11.1999 | Lok Altmark Stendal | - | Rot-Weiß Erfurt | 1:1 | ||||
| 16. Ronde | 05.12.1999 | Hertha BSC II | - | Lok Altmark Stendal | 1:1 | ||||
| 17. Ronde | 12.12.1999 | Lok Altmark Stendal | - | VfL Halle 96 | 1:0 |
Bulgarije