| Bundesliga Round 1 | Bundesliga Round 2 |
| 14 August 1999 | 21 August 1999 |
| Wolfsburg | 2-1 | 1860 Munich | Unterhaching | 2-0 | Duisburg |
| Duisburg | 0-0 | Leverkusen | Bielefeld | 1-1 | Berlin |
| Kaiserslautern | 1-0 | Dortmund | Hamburg | 3-0 | Stuttgart |
| Schalke | 1-1 | Bielefeld | Bremen | 0-1 | Schalke |
| Stuttgart | 0-0 | Bremen | Dortmund | 2-1 | Wolfsburg |
| Bayern Munich | 2-2 | Hamburg | 1860 Munich | 4-1 | Ulm |
| Frankfurt | 3-0 | Unterhaching | Freiburg | 2-3 | Frankfurt |
| Ulm | 1-1 | Freiburg | Rostock | 4-2 | Kaiserslautern |
| Berlin | 5-2 | Rostock | Leverkusen | 2-0 | Bayern Munich |
| Bundesliga Round 3 | Bundesliga Round 4 |
| 28 August 1999 | 11 September 1999 |
| Kaiserslautern | 0-2 | Bielefeld | Bielefeld | 0-0 | Wolfsburg |
| Schalke | 1-3 | Hamburg | Rostock | 2-1 | Ulm |
| Wolfsburg | 2-0 | Rostock | Unterhaching | 2-0 | Stuttgart |
| Berlin | 1-1 | Bremen | Hamburg | 5-1 | Berlin |
| Stuttgart | 1-2 | Leverkusen | Dortmund | 1-1 | Freiburg |
| Bayern Munich | 1-0 | Unterhaching | Duisburg | 1-2 | Bayern Munich |
| Freiburg | 3-0 | 1860 Munich | Leverkusen | 3-2 | Schalke |
| Frankfurt | 2-2 | Duisburg | 1860 Munich | 2-0 | Frankfurt |
| Ulm | 0-1 | Dortmund | Bremen | 5-0 | Kaiserslautern |
| Bundesliga Round 5 | Bundesliga Round 6 |
| 18 September 1999 | 25 September 1999 |
| Ulm | 2-0 | Bielefeld | Unterhaching | 1-1 | Berlin |
| Freiburg | 5-0 | Rostock | Hamburg | 2-2 | Wolfsburg |
| Wolfsburg | 2-7 | Bremen | Bremen | 2-2 | Ulm |
| Kaiserslautern | 2-0 | Hamburg | Bielefeld | 2-1 | Freiburg |
| Berlin | 0-0 | Leverkusen | Rostock | 0-0 | 1860 Munich |
| Schalke | 1-0 | Unterhaching | Dortmund | 1-0 | Frankfurt |
| Stuttgart | 4-2 | Duisburg | Bayern Munich | 0-1 | Stuttgart |
| 1860 Munich | 0-3 | Dortmund | Duisburg | 1-1 | Schalke |
| Frankfurt | 1-2 | Bayern Munich | Leverkusen | 3-1 | Kaiserslautern |
| Bundesliga Round 7 | Bundesliga Round 8 |
| 2 October 1999 | 16 October 1999 |
| 1860 Munich | 5-0 | Bielefeld | Unterhaching | 1-1 | Wolfsburg |
| Ulm | 1-2 | Hamburg | Hamburg | 2-0 | Freiburg |
| Wolfsburg | 3-1 | Leverkusen | Bremen | 1-3 | 1860 Munich |
| Kaiserslautern | 4-2 | Unterhaching | Bielefeld | 0-2 | Dortmund |
| Berlin | 2-1 | Duisburg | Rostock | 3-1 | Frankfurt |
| Schalke | 1-1 | Bayern Munich | Stuttgart | 0-2 | Schalke |
| Dortmund | 3-0 | Rostock | Bayern Munich | 3-1 | Berlin |
| Freiburg | 2-1 | Bremen | Duisburg | 2-2 | Kaiserslautern |
| Frankfurt | 0-1 | Stuttgart | Leverkusen | 4-1 | Ulm |
| Bundesliga Round 9 | Bundesliga Round 10 |
| 23 October 1999 | 30 October 1999 |
| Ulm | 1-0 | Unterhaching | Bremen | 2-1 | Rostock |
| Wolfsburg | 1-0 | Duisburg | Bielefeld | 1-1 | Frankfurt |
| Kaiserslautern | 0-2 | Bayern Munich | Hamburg | 1-1 | Dortmund |
| Berlin | 1-1 | Stuttgart | Schalke | 1-1 | Berlin |
| Rostock | 2-1 | Bielefeld | Stuttgart | 0-1 | Kaiserslautern |
| Dortmund | 1-3 | Bremen | Bayern Munich | 5-0 | Wolfsburg |
| 1860 Munich | 0-0 | Hamburg | Leverkusen | 1-1 | 1860 Munich |
| Freiburg | 0-0 | Leverkusen | Unterhaching | 1-0 | Freiburg |
| Frankfurt | 0-2 | Schalke | Duisburg | 0-0 | Ulm |
| Bundesliga Round 11 | Bundesliga Round 12 |
| 6 November 1999 | 20 November 1999 |
| Ulm | 0-1 | Bayern Munich | Unterhaching | 1-0 | Dortmund |
| Wolfsburg | 0-2 | Stuttgart | Hamburg | 5-0 | Bielefeld |
| Kaiserslautern | 2-1 | Schalke | Bremen | 3-1 | Frankfurt |
| Bielefeld | 2-2 | Bremen | Berlin | 0-1 | Kaiserslautern |
| Rostock | 3-3 | Hamburg | Schalke | 1-1 | Wolfsburg |
| Dortmund | 1-1 | Leverkusen | Stuttgart | 2-0 | Ulm |
| 1860 Munich | 2-1 | Unterhaching | Bayern Munich | 6-1 | Freiburg |
| Freiburg | 3-0 | Duisburg | Duisburg | 3-0 | 1860 Munich |
| Frankfurt | 4-0 | Berlin | Leverkusen | 1-1 | Rostock |
| Bundesliga Round 13 | Bundesliga Round 14 |
| 27 November 1999 | 4 December 1999 |
| Ulm | 1-1 | Schalke | Unterhaching | 2-0 | Bielefeld |
| Freiburg | 0-2 | Stuttgart | Berlin | 3-0 | Ulm |
| Wolfsburg | 2-3 | Berlin | Kaiserslautern | 2-2 | Wolfsburg |
| Bremen | 2-1 | Hamburg | Schalke | 2-2 | Freiburg |
| Bielefeld | 1-2 | Leverkusen | Stuttgart | 1-3 | 1860 Munich |
| Rostock | 1-1 | Unterhaching | Bayern Munich | 1-1 | Dortmund |
| Dortmund | 2-2 | Duisburg | Leverkusen | 3-2 | Bremen |
| 1860 Munich | 1-0 | Bayern Munich | Duisburg | 2-2 | Rostock |
| Frankfurt | 0-1 | Kaiserslautern | Hamburg | 1-0 | Frankfurt |
| Bundesliga Round 15 | Bundesliga Round 16 |
| 11 December 1999 | 15 December 1999 |
| Ulm | 3-1 | Kaiserslautern | Unterhaching | 1-1 | Hamburg |
| Wolfsburg | 1-0 | Frankfurt | Wolfsburg | 1-2 | Ulm |
| Bremen | 2-2 | Unterhaching | Kaiserslautern | 0-2 | Freiburg |
| Bielefeld | 0-1 | Duisburg | Berlin | 1-1 | 1860 Munich |
| Rostock | 0-3 | Bayern Munich | Schalke | 0-0 | Dortmund |
| Dortmund | 1-1 | Stuttgart | Stuttgart | 3-1 | Rostock |
| 1860 Munich | 3-3 | Schalke | Bayern Munich | 2-1 | Bielefeld |
| Freiburg | 0-1 | Berlin | Duisburg | 0-1 | Bremen |
| Leverkusen | 2-2 | Hamburg | Frankfurt | 1-2 | Leverkusen |
| Bundesliga Round 17 |
| 18 December 1999 |
| Ulm | 3-0 | Frankfurt |
| Hamburg | 6-1 | Duisburg |
| Bremen | 0-2 | Bayern Munich |
| Bielefeld | 1-2 | Stuttgart |
| Rostock | 1-0 | Schalke |
| Dortmund | 4-0 | Berlin |
| 1860 Munich | 2-1 | Kaiserslautern |
| Freiburg | 1-1 | Wolfsburg |
| Leverkusen | 2-1 | Unterhaching |
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