| 1 | 15.08.1999 17:30 | Hertha BSC |
– |  FC Hansa Rostock |
5 : 2 | |
| 2 | 20.08.1999 20:00 | Arminia Bielefeld |
– | Hertha BSC |
1 : 1 | |
| 3 | 28.08.1999 15:30 | Hertha BSC |
– |  SV Werder Bremen |
1 : 1 | |
| 4 | 11.09.1999 15:30 | Hamburger SV |
– | Hertha BSC |
5 : 1 | |
| 5 | 18.09.1999 15:30 | Hertha BSC |
– |  Bayer 04 Leverkusen |
0 : 0 | |
| 6 | 25.09.1999 15:30 | SpVgg Unterhaching |
– | Hertha BSC |
1 : 1 | |
| 7 | 02.10.1999 15:30 | Hertha BSC |
– |  MSV Duisburg |
2 : 1 | |
| 8 | 16.10.1999 15:30 | FC Bayern München |
– | Hertha BSC |
3 : 1 | |
| 9 | 23.10.1999 15:30 | Hertha BSC |
– |  VfB Stuttgart |
1 : 1 | |
| 10 | 30.10.1999 15:30 | FC Schalke 04 |
– | Hertha BSC |
1 : 1 | |
| 11 | 06.11.1999 15:30 | Eintracht Frankfurt |
– | Hertha BSC |
4 : 0 | |
| 12 | 20.11.1999 15:30 | Hertha BSC |
– |  1. FC Kaiserslautern |
0 : 1 | |
| 13 | 27.11.1999 15:30 | VfL Wolfsburg |
– | Hertha BSC |
2 : 3 | |
| 14 | 04.12.1999 15:30 | Hertha BSC |
– |  SSV Ulm 1846 |
3 : 0 | |
| 15 | 11.12.1999 15:30 | SC Freiburg |
– | Hertha BSC |
0 : 1 | |
| 16 | 14.12.1999 20:00 | Hertha BSC |
– |  TSV 1860 München |
1 : 1 | |
| 17 | 19.12.1999 20:00 | Borussia Dortmund |
– | Hertha BSC |
4 : 0 | |
| 18 | 04.02.2000 20:00 | FC Hansa Rostock |
– | Hertha BSC |
0 : 1 | |
| 19 | 08.02.2000 20:00 | Hertha BSC |
– | Arminia Bielefeld |
2 : 0 | |
| 20 | 11.02.2000 20:00 | SV Werder Bremen |
– | Hertha BSC |
4 : 1 | |
| 21 | 18.02.2000 20:00 | Hertha BSC |
– | Hamburger SV |
2 : 1 | |
| 22 | 26.02.2000 15:30 | Bayer 04 Leverkusen |
– | Hertha BSC |
3 : 1 | |
| 23 | 04.03.2000 15:30 | Hertha BSC |
– | SpVgg Unterhaching |
2 : 1 | |
| 24 | 11.03.2000 15:30 | MSV Duisburg |
– | Hertha BSC |
0 : 0 | |
| 25 | 18.03.2000 15:30 | Hertha BSC |
– | FC Bayern München |
1 : 1 | |
| 26 | 25.03.2000 15:30 | VfB Stuttgart |
– | Hertha BSC |
1 : 0 | |
| 27 | 01.04.2000 15:30 | Hertha BSC |
– | FC Schalke 04 |
2 : 1 | |
| 28 | 08.04.2000 15:30 | Hertha BSC |
– | Eintracht Frankfurt |
1 : 0 | |
| 29 | 11.04.2000 20:00 | 1. FC Kaiserslautern |
– | Hertha BSC |
1 : 2 | |
| 30 | 14.04.2000 20:00 | Hertha BSC |
– | VfL Wolfsburg |
0 : 0 | |
| 31 | 22.04.2000 15:30 | SSV Ulm 1846 |
– | Hertha BSC |
0 : 1 | |
| 32 | 28.04.2000 20:00 | Hertha BSC |
– | SC Freiburg |
0 : 0 | |
| 33 | 13.05.2000 15:30 | TSV 1860 München |
– | Hertha BSC |
2 : 1 | |
| 34 | 20.05.2000 15:30 | Hertha BSC |
– | Borussia Dortmund |
0 : 3 |