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| 24/09/1999 | 18:00 | VfL Bochum | - | SpVgg Greuther Fürth | 1:2 (0:1) | |
| 18:00 | 1. FC Nürnberg | - | Chemnitzer FC | 1:0 (1:0) | ||
| 18:00 | 1. FSV Mainz 05 | - | Hannover 96 | 1:0 (0:0) | ||
| 25/09/1999 | 14:30 | Fortuna Köln | - | Karlsruher SC | 2:3 (1:1) | |
| 26/09/1999 | 14:00 | Waldhof Mannheim | - | FC St. Pauli | 1:3 (1:1) | |
| 14:00 | TeBe Berlin | - | Rot-Weiß Oberhausen | 1:0 (1:0) | ||
| 14:00 | Stuttgarter Kickers | - | Energie Cottbus | 1:0 (0:0) | ||
| 14:00 | Kickers Offenbach | - | Alemannia Aachen | 1:2 (0:0) | ||
| 27/09/1999 | 19:15 | Bor. Mönchengladbach | - | 1. FC Köln | 3:1 (0:1) |
| » Tables | Home | Away | First round | Second round | First half | Second half |
| # | Team | M. | W | D | L | goals | Dif. | Pt. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
1. FC Nürnberg | 6 | 4 | 1 | 1 | 10:5 | 5 | 13 |
| 2 |
|
Alemannia Aachen | 6 | 4 | 1 | 1 | 12:11 | 1 | 13 |
| 3 |
|
Energie Cottbus | 6 | 4 | 0 | 2 | 11:2 | 9 | 12 |
| 4 |
|
TeBe Berlin | 6 | 3 | 3 | 0 | 11:7 | 4 | 12 |
| 5 |
|
SpVgg Greuther Fürth | 6 | 3 | 3 | 0 | 7:4 | 3 | 12 |
| 6 |
|
1. FC Köln | 6 | 3 | 2 | 1 | 10:7 | 3 | 11 |
| 7 |
|
Hannover 96 | 6 | 3 | 1 | 2 | 12:9 | 3 | 10 |
| 8 |
|
Karlsruher SC | 6 | 2 | 3 | 1 | 11:9 | 2 | 9 |
| 9 |
|
Stuttgarter Kickers | 6 | 2 | 2 | 2 | 7:11 | -4 | 8 |
| 10 |
|
VfL Bochum | 6 | 2 | 1 | 3 | 11:9 | 2 | 7 |
| 11 |
|
Chemnitzer FC | 6 | 2 | 1 | 3 | 6:7 | -1 | 7 |
| 12 |
|
Bor. Mönchengladbach | 6 | 2 | 0 | 4 | 8:11 | -3 | 6 |
| 13 |
|
1. FSV Mainz 05 | 6 | 1 | 3 | 2 | 5:8 | -3 | 6 |
| 14 |
|
Fortuna Köln | 6 | 2 | 0 | 4 | 7:11 | -4 | 6 |
| 15 |
|
Waldhof Mannheim | 6 | 1 | 2 | 3 | 9:11 | -2 | 5 |
| 16 |
|
FC St. Pauli | 6 | 1 | 2 | 3 | 4:7 | -3 | 5 |
| 17 |
|
Rot-Weiß Oberhausen | 6 | 1 | 1 | 4 | 8:12 | -4 | 4 |
| 18 |
|
Kickers Offenbach | 6 | 0 | 2 | 4 | 4:12 | -8 | 2 |
