 |
 |
|
| 12/06/1999 | SG Wattenscheid 09 | - | FC Schalke 04 | 3:1 | ||
| Rot-Weiß Erfurt | - | FSV Salmrohr | 2:3 aet | |||
| 13/06/1999 | SC Vahr-Blockdiek | - | TeBe Berlin | 0:6 | ||
| VfL Bochum | - | Hannover 96 | 2:3 | |||
| Fortuna Düsseldorf | - | 1. FC Köln | 2:5 | |||
| VfB Leipzig | - | Hamburger SV | 3:0 | |||
| Holstein Kiel | - | 1. FC Magdeburg | 2:4 aet | |||
| VfL Osnabrück | - | VfL Wolfsburg | 4:2 | |||
| Hansa Rostock | - | Energie Cottbus | 0:3 | |||
| SC Freiburg | - | Eintracht Frankfurt | 7:1 | |||
| FV Dresden-Nord | - | FC 08 Homburg | 7:1 | |||
| Dynamo Dresden | - | 1. FSV Mainz 05 | 4:0 | |||
| Freiburger FC | - | FC Augsburg | 0:4 | |||
| FK Pirmasens | - | SG 01 Hoechst | 5:3 pso | |||
| 1. FC Saarbrücken | - | Waldhof Mannheim | 3:0 | |||
| SV Darmstadt 98 | - | Stuttgarter Kickers | 3:2 |
