| Fr., 15.10.1999 | SC Fortuna Köln - FC St. Pauli | 2:0 |
| Fr., 15.10.1999 | Borussia Mönchengladbach - SpVgg Greuther Fürth | 2:0 |
| Fr., 15.10.1999 | Kickers Offenbach - 1. FC Köln | 0:1 |
| Sa., 16.10.1999 | VfL Bochum - FC Energie Cottbus | 2:4 |
| So., 17.10.1999 | Chemnitzer FC - Hannover 96 | 2:1 |
| So., 17.10.1999 | SV Waldhof Mannheim - Rot-Weiß Oberhausen | 2:0 |
| So., 17.10.1999 | Tennis Borussia Berlin - Stuttgarter Kickers | 2:0 |
| So., 17.10.1999 | FSV Mainz 05 - Alemannia Aachen | 4:2 |
| Mo., 18.10.1999 | 1. FC Nürnberg - Karlsruher SC | 4:3 |
| Sp. | S-U-N | Tore | Diff. | P | ||||
|---|---|---|---|---|---|---|---|---|
| 1. |  |  | 1. FC Köln | 8 | 5-2-1 | 14:7 | 7 | 17 |
| 2. | |  | 1. FC Nürnberg | 8 | 5-1-2 | 14:10 | 4 | 16 |
| 3. | |  | FC Energie Cottbus | 8 | 5-0-3 | 17:8 | 9 | 15 |
| 4. | |  | Tennis Borussia Berlin | 8 | 4-3-1 | 13:9 | 4 | 15 |
| 5. |  |  | SpVgg Greuther Fürth | 8 | 4-3-1 | 9:6 | 3 | 15 |
| 6. | |  | Alemannia Aachen | 8 | 4-2-2 | 15:16 | -1 | 14 |
| 7. | |  | Hannover 96 | 8 | 4-1-3 | 15:11 | 4 | 13 |
| 8. |  |  | Chemnitzer FC | 8 | 4-1-3 | 12:10 | 2 | 13 |
| 9. | |  | FSV Mainz 05 | 8 | 3-3-2 | 11:11 | 0 | 12 |
| 10. | |  | Borussia Mönchengladbach | 8 | 3-1-4 | 11:12 | -1 | 10 |
| 11. | |  | SC Fortuna Köln | 8 | 3-1-4 | 10:12 | -2 | 10 |
| 12. | |  | Karlsruher SC | 8 | 2-3-3 | 15:15 | 0 | 9 |
| 13. | |  | Stuttgarter Kickers | 8 | 2-3-3 | 7:13 | -6 | 9 |
| 14. | |  | VfL Bochum | 8 | 2-2-4 | 13:13 | 0 | 8 |
| 15. | |  | SV Waldhof Mannheim | 8 | 2-2-4 | 11:14 | -3 | 8 |
| 16. | |  | FC St. Pauli | 8 | 1-3-4 | 5:10 | -5 | 6 |
| 17. | |  | Rot-Weiß Oberhausen | 8 | 1-2-5 | 9:15 | -6 | 5 |
| 18. | |  | Kickers Offenbach | 8 | 0-3-5 | 5:14 | -9 | 3 |