| Fr., 01.10.1999 | 1. FC Köln - SV Waldhof Mannheim | 3:0 |
| Fr., 01.10.1999 | FC St. Pauli - Kickers Offenbach | 1:1 |
| Fr., 01.10.1999 | Alemannia Aachen - SC Fortuna Köln | 1:1 |
| Sa., 02.10.1999 | Karlsruher SC - FSV Mainz 05 | 1:2 |
| So., 03.10.1999 | FC Energie Cottbus - Chemnitzer FC | 2:4 |
| So., 03.10.1999 | Stuttgarter Kickers - VfL Bochum | 0:0 |
| So., 03.10.1999 | SpVgg Greuther Fürth - Tennis Borussia Berlin | 2:0 |
| So., 03.10.1999 | Rot-Weiß Oberhausen - Borussia Mönchengladbach | 1:1 |
| Mo., 04.10.1999 | Hannover 96 - 1. FC Nürnberg | 2:0 |
| Sp. | S-U-N | Tore | Diff. | P | ||||
|---|---|---|---|---|---|---|---|---|
| 1. |  |  | SpVgg Greuther Fürth | 7 | 4-3-0 | 9:4 | 5 | 15 |
| 2. | |  | 1. FC Köln | 7 | 4-2-1 | 13:7 | 6 | 14 |
| 3. |  |  | Alemannia Aachen | 7 | 4-2-1 | 13:12 | 1 | 14 |
| 4. | |  | Hannover 96 | 7 | 4-1-2 | 14:9 | 5 | 13 |
| 5. | |  | 1. FC Nürnberg | 7 | 4-1-2 | 10:7 | 3 | 13 |
| 6. | |  | FC Energie Cottbus | 7 | 4-0-3 | 13:6 | 7 | 12 |
| 7. | |  | Tennis Borussia Berlin | 7 | 3-3-1 | 11:9 | 2 | 12 |
| 8. | |  | Chemnitzer FC | 7 | 3-1-3 | 10:9 | 1 | 10 |
| 9. | |  | Karlsruher SC | 7 | 2-3-2 | 12:11 | 1 | 9 |
| 10. | |  | FSV Mainz 05 | 7 | 2-3-2 | 7:9 | -2 | 9 |
| 11. | |  | Stuttgarter Kickers | 7 | 2-3-2 | 7:11 | -4 | 9 |
| 12. | |  | VfL Bochum | 7 | 2-2-3 | 11:9 | 2 | 8 |
| 13. | |  | Borussia Mönchengladbach | 7 | 2-1-4 | 9:12 | -3 | 7 |
| 14. |  |  | SC Fortuna Köln | 7 | 2-1-4 | 8:12 | -4 | 7 |
| 15. | |  | FC St. Pauli | 7 | 1-3-3 | 5:8 | -3 | 6 |
| 16. | |  | Rot-Weiß Oberhausen | 7 | 1-2-4 | 9:13 | -4 | 5 |
| 17. | |  | SV Waldhof Mannheim | 7 | 1-2-4 | 9:14 | -5 | 5 |
| 18. | |  | Kickers Offenbach | 7 | 0-3-4 | 5:13 | -8 | 3 |