| Fr., 10.09.1999 | SV Waldhof Mannheim - Karlsruher SC | 1:1 |
| Fr., 10.09.1999 | Tennis Borussia Berlin - FC St. Pauli | 2:0 |
| Fr., 10.09.1999 | Kickers Offenbach - Hannover 96 | 0:2 |
| Sa., 11.09.1999 | Borussia Mönchengladbach - Alemannia Aachen | 1:2 |
| So., 12.09.1999 | SC Fortuna Köln - Chemnitzer FC | 1:0 |
| So., 12.09.1999 | Stuttgarter Kickers - Rot-Weiß Oberhausen | 2:2 |
| So., 12.09.1999 | SpVgg Greuther Fürth - FC Energie Cottbus | 1:0 |
| So., 12.09.1999 | FSV Mainz 05 - 1. FC Nürnberg | 1:1 |
| Mo., 13.09.1999 | VfL Bochum - 1. FC Köln | 2:3 |
| Sp. | S-U-N | Tore | Diff. | P | ||||
|---|---|---|---|---|---|---|---|---|
| 1. |  |  | 1. FC Nürnberg | 4 | 3-1-0 | 9:3 | 6 | 10 |
| 2. | |  | 1. FC Köln | 4 | 3-1-0 | 8:3 | 5 | 10 |
| 3. |  |  | FC Energie Cottbus | 4 | 3-0-1 | 9:1 | 8 | 9 |
| 4. | |  | Tennis Borussia Berlin | 4 | 2-2-0 | 9:6 | 3 | 8 |
| 5. | |  | SpVgg Greuther Fürth | 4 | 2-2-0 | 5:3 | 2 | 8 |
| 6. | |  | VfL Bochum | 4 | 2-1-1 | 10:4 | 6 | 7 |
| 7. | |  | Hannover 96 | 4 | 2-1-1 | 9:7 | 2 | 7 |
| 8. | |  | Alemannia Aachen | 4 | 2-1-1 | 8:9 | -1 | 7 |
| 9. | |  | Chemnitzer FC | 4 | 2-0-2 | 5:5 | 0 | 6 |
| 10. | |  | SC Fortuna Köln | 4 | 2-0-2 | 4:5 | -1 | 6 |
| 11. | |  | SV Waldhof Mannheim | 4 | 1-2-1 | 7:6 | 1 | 5 |
| 12. | |  | Karlsruher SC | 4 | 1-2-1 | 7:6 | 1 | 5 |
| 13. |  |  | Stuttgarter Kickers | 4 | 1-1-2 | 6:11 | -5 | 4 |
| 14. | |  | FC St. Pauli | 4 | 0-2-2 | 1:4 | -3 | 2 |
| 15. | |  | FSV Mainz 05 | 4 | 0-2-2 | 3:7 | -4 | 2 |
| 16. | |  | Rot-Weiß Oberhausen | 4 | 0-1-3 | 5:11 | -6 | 1 |
| 17. | |  | Kickers Offenbach | 4 | 0-1-3 | 2:9 | -7 | 1 |
| 18. | |  | Borussia Mönchengladbach | 4 | 0-0-4 | 3:10 | -7 | 0 |