1. Round | 13/08/1999 | VfL Wolfsburg | - | TSV 1860 München | 2:1 | ||||
2. Round | 21/08/1999 | TSV 1860 München | - | SSV Ulm 1846 | 4:1 | ||||
3. Round | 28/08/1999 | SC Freiburg | - | TSV 1860 München | 3:0 | ![]() |
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4. Round | 12/09/1999 | TSV 1860 München | - | Eintracht Frankfurt | 2:0 | ||||
5. Round | 17/09/1999 | TSV 1860 München | - | Borussia Dortmund | 0:3 | ||||
7. Round | 01/10/1999 | TSV 1860 München | - | Arminia Bielefeld | 5:0 | ||||
9. Round | 23/10/1999 | TSV 1860 München | - | Hamburger SV | 0:0 | ||||
11. Round | 06/11/1999 | TSV 1860 München | - | SpVgg Unterhaching | 2:1 | ||||
15. Round | 11/12/1999 | TSV 1860 München | - | FC Schalke 04 | 3:3 | ||||
17. Round | 18/12/1999 | TSV 1860 München | - | 1. FC Kaiserslautern | 2:1 |