| Fr., 17.09.1999 | FC St. Pauli - Borussia Mönchengladbach | 0:2 |
| Fr., 17.09.1999 | Karlsruher SC - Kickers Offenbach | 1:1 |
| Fr., 17.09.1999 | Rot-Weiß Oberhausen - VfL Bochum | 3:0 |
| Sa., 18.09.1999 | Chemnitzer FC - FSV Mainz 05 | 1:1 |
| So., 19.09.1999 | Alemannia Aachen - SV Waldhof Mannheim | 2:1 |
| So., 19.09.1999 | Hannover 96 - SC Fortuna Köln | 3:1 |
| So., 19.09.1999 | SpVgg Greuther Fürth - Stuttgarter Kickers | 0:0 |
| So., 19.09.1999 | FC Energie Cottbus - 1. FC Nürnberg | 2:0 |
| Mo., 20.09.1999 | 1. FC Köln - Tennis Borussia Berlin | 1:1 |
| Sp. | S-U-N | Tore | Diff. | P | ||||
|---|---|---|---|---|---|---|---|---|
| 1. |  |  | FC Energie Cottbus | 5 | 4-0-1 | 11:1 | 10 | 12 |
| 2. |  |  | 1. FC Köln | 5 | 3-2-0 | 9:4 | 5 | 11 |
| 3. | |  | Hannover 96 | 5 | 3-1-1 | 12:8 | 4 | 10 |
| 4. |  |  | 1. FC Nürnberg | 5 | 3-1-1 | 9:5 | 4 | 10 |
| 5. | |  | Alemannia Aachen | 5 | 3-1-1 | 10:10 | 0 | 10 |
| 6. | |  | Tennis Borussia Berlin | 5 | 2-3-0 | 10:7 | 3 | 9 |
| 7. | |  | SpVgg Greuther Fürth | 5 | 2-3-0 | 5:3 | 2 | 9 |
| 8. | |  | VfL Bochum | 5 | 2-1-2 | 10:7 | 3 | 7 |
| 9. | |  | Chemnitzer FC | 5 | 2-1-2 | 6:6 | 0 | 7 |
| 10. | |  | Karlsruher SC | 5 | 1-3-1 | 8:7 | 1 | 6 |
| 11. | |  | SC Fortuna Köln | 5 | 2-0-3 | 5:8 | -3 | 6 |
| 12. | |  | SV Waldhof Mannheim | 5 | 1-2-2 | 8:8 | 0 | 5 |
| 13. | |  | Stuttgarter Kickers | 5 | 1-2-2 | 6:11 | -5 | 5 |
| 14. | |  | Rot-Weiß Oberhausen | 5 | 1-1-3 | 8:11 | -3 | 4 |
| 15. | |  | FSV Mainz 05 | 5 | 0-3-2 | 4:8 | -4 | 3 |
| 16. | |  | Borussia Mönchengladbach | 5 | 1-0-4 | 5:10 | -5 | 3 |
| 17. | |  | FC St. Pauli | 5 | 0-2-3 | 1:6 | -5 | 2 |
| 18. | |  | Kickers Offenbach | 5 | 0-2-3 | 3:10 | -7 | 2 |