| Fr., 22.10.1999 | Alemannia Aachen - 1. FC Nürnberg | 3:1 |
| Fr., 22.10.1999 | Rot-Weiß Oberhausen - Kickers Offenbach | 1:0 |
| Fr., 22.10.1999 | FC Energie Cottbus - Hannover 96 | 1:0 |
| Sa., 23.10.1999 | Stuttgarter Kickers - Borussia Mönchengladbach | 3:1 |
| So., 24.10.1999 | Karlsruher SC - Chemnitzer FC | 1:2 |
| So., 24.10.1999 | FC St. Pauli - FSV Mainz 05 | 2:2 |
| So., 24.10.1999 | VfL Bochum - Tennis Borussia Berlin | 2:6 |
| So., 24.10.1999 | SpVgg Greuther Fürth - SV Waldhof Mannheim | 0:0 |
| Mo., 25.10.1999 | 1. FC Köln - SC Fortuna Köln | 3:0 |
| Sp. | S-U-N | Tore | Diff. | P | ||||
|---|---|---|---|---|---|---|---|---|
| 1. |  |  | 1. FC Köln | 9 | 6-2-1 | 17:7 | 10 | 20 |
| 2. |  |  | FC Energie Cottbus | 9 | 6-0-3 | 18:8 | 10 | 18 |
| 3. | |  | Tennis Borussia Berlin | 9 | 5-3-1 | 19:11 | 8 | 18 |
| 4. | |  | Alemannia Aachen | 9 | 5-2-2 | 18:17 | 1 | 17 |
| 5. | |  | Chemnitzer FC | 9 | 5-1-3 | 14:11 | 3 | 16 |
| 6. |  |  | SpVgg Greuther Fürth | 9 | 4-4-1 | 9:6 | 3 | 16 |
| 7. | |  | 1. FC Nürnberg | 9 | 5-1-3 | 15:13 | 2 | 16 |
| 8. | |  | Hannover 96 | 9 | 4-1-4 | 15:12 | 3 | 13 |
| 9. | |  | FSV Mainz 05 | 9 | 3-4-2 | 13:13 | 0 | 13 |
| 10. | |  | Stuttgarter Kickers | 9 | 3-3-3 | 10:14 | -4 | 12 |
| 11. | |  | Borussia Mönchengladbach | 9 | 3-1-5 | 12:15 | -3 | 10 |
| 12. | |  | SC Fortuna Köln | 9 | 3-1-5 | 10:15 | -5 | 10 |
| 13. | |  | Karlsruher SC | 9 | 2-3-4 | 16:17 | -1 | 9 |
| 14. | |  | SV Waldhof Mannheim | 9 | 2-3-4 | 11:14 | -3 | 9 |
| 15. | |  | VfL Bochum | 9 | 2-2-5 | 15:19 | -4 | 8 |
| 16. | |  | Rot-Weiß Oberhausen | 9 | 2-2-5 | 10:15 | -5 | 8 |
| 17. | |  | FC St. Pauli | 9 | 1-4-4 | 7:12 | -5 | 7 |
| 18. | |  | Kickers Offenbach | 9 | 0-3-6 | 5:15 | -10 | 3 |