| 1. Round | 30/07/1999 | VfR Mannheim | - | FSV Frankfurt | 2:1 | ||||
| 2. Round | 07/08/1999 | FSV Frankfurt | - | Quelle Fürth | 1:0 | ||||
| 3. Round | 15/08/1999 | SC Pfullendorf | - | FSV Frankfurt | 3:2 | ||||
| 4. Round | 20/08/1999 | FSV Frankfurt | - | SV Darmstadt 98 | 3:2 | ||||
| 5. Round | 27/08/1999 | Wacker Burghausen | - | FSV Frankfurt | 1:0 | ||||
| 6. Round | 31/08/1999 | FSV Frankfurt | - | Karlsruher SC II | 2:0 | ||||
| 8. Round | 11/09/1999 | FSV Frankfurt | - | FC Augsburg | 3:0 | ||||
| 9. Round | 18/09/1999 | Borussia Fulda | - | FSV Frankfurt | 1:2 |  |
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| 10. Round | 26/09/1999 | FSV Frankfurt | - | 1. FC Schweinfurt 05 | 1:1 | ||||
| 12. Round | 09/10/1999 | FSV Frankfurt | - | SV Wehen-Taunusstein | 0:0 |  |
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| 15. Round | 31/10/1999 | Bayern München II | - | FSV Frankfurt | 5:2 | ||||
| 16. Round | 07/11/1999 | FSV Frankfurt | - | SSV Reutlingen | 0:5 | ||||
| 17. Round | 13/11/1999 | VfB Stuttgart II | - | FSV Frankfurt | 0:0 | ||||
| 19. Round | 27/11/1999 | Quelle Fürth | - | FSV Frankfurt | 3:2 | ||||
| 27. Round | 16/04/2000 | 1. FC Schweinfurt 05 | - | FSV Frankfurt | 1:1 | ||||
| 30. Round | 07/05/2000 | FSV Frankfurt | - | SV Lohhof | 4:2 | |
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| 34. Round | 27/05/2000 | FSV Frankfurt | - | VfB Stuttgart II | 0:2 dec. |
Portugal