| 2. Round | 22/08/1999 | Fortuna Köln | - | 1. FSV Mainz 05 | 2:1 | ||||
| 5. Round | 18/09/1999 | Chemnitzer FC | - | 1. FSV Mainz 05 | 1:1 | ||||
| 20. Round | 26/02/2000 | 1. FSV Mainz 05 | - | Energie Cottbus | 1:0 | ||||
| 21. Round | 04/03/2000 | 1. FC Nürnberg | - | 1. FSV Mainz 05 | 2:0 | ||||
| 25. Round | 02/04/2000 | Alemannia Aachen | - | 1. FSV Mainz 05 | 1:0 | ||||
| 26. Round | 07/04/2000 | 1. FSV Mainz 05 | - | FC St. Pauli | 1:1 | ||||
| 29. Round | 30/04/2000 | SpVgg Greuther Fürth | - | 1. FSV Mainz 05 | 2:0 | ||||
| 30. Round | 07/05/2000 | 1. FSV Mainz 05 | - | Stuttgarter Kickers | 2:0 | ||||
| 31. Round | 15/05/2000 | VfL Bochum | - | 1. FSV Mainz 05 | 0:1 | ||||
| 33. Round | 21/05/2000 | Bor. Mönchengladbach | - | 1. FSV Mainz 05 | 6:1 |  |
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| 34. Round | 26/05/2000 | 1. FSV Mainz 05 | - | Waldhof Mannheim | 2:0 |
Scotland