| 1. Round | 15/08/1999 | Alemannia Aachen | - | Stuttgarter Kickers | 4:1 | ||||
| 2. Round | 20/08/1999 | VfL Bochum | - | Alemannia Aachen | 5:0 | ||||
| 3. Round | 28/08/1999 | Alemannia Aachen | - | TeBe Berlin | 2:2 |  |
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| 4. Round | 11/09/1999 | Bor. Mönchengladbach | - | Alemannia Aachen | 1:2 | ||||
| 6. Round | 26/09/1999 | Kickers Offenbach | - | Alemannia Aachen | 1:2 | ||||
| 7. Round | 01/10/1999 | Alemannia Aachen | - | Fortuna Köln | 1:1 | ||||
| 8. Round | 17/10/1999 | 1. FSV Mainz 05 | - | Alemannia Aachen | 4:2 |
Germany