| Union Berlin beat Carl Zeiss Jena 1-0 (A) on 25 Sep 1999 |
| Carl Zeiss Jena beat Erzgebirge Aue 2-1 (A) on 11 Sep 1999 |
| Erzgebirge Aue beat VFC Plauen 3-0 (H) on 25 Aug 1999 |
| VFC Plauen beat Dresdner 3-1 (H) on 26 Sep 1999 |
| Dresdner beat VfL Halle 96 3-0 (H) on 7 Sep 1999 |
| VfL Halle 96 beat VfB Leipzig 2-1 (H) on 11 Sep 1999 |
| VfB Leipzig beat Magdeburg 1-0 (A) on 20 Aug 1999 |
| Magdeburg beat Hertha BSC II 3-0 (H) on 19 Sep 1999 |
| Hertha BSC II beat FSV Zwickau 4-1 (H) on 24 Sep 1999 |
| FSV Zwickau beat Stahl Eisenhüttenstadt 4-0 (H) on 6 Aug 1999 |
| Stahl Eisenhüttenstadt beat Sachsen Leipzig 1-0 (H) on 7 Sep 1999 |
| Sachsen Leipzig beat Lok Altmark Stendal 3-2 (A) on 15 Aug 1999 |
| Lok Altmark Stendal beat SV Babelsberg 03 1-0 (H) on 25 Aug 1999 |
| SV Babelsberg 03 beat TeBe Berlin II 3-2 (H) on 21 Aug 1999 |
| TeBe Berlin II beat Rot Weiß Erfurt 3-2 (H) on 7 Sep 1999 |
| Rot Weiß Erfurt beat BFC Dynamo 1-0 (H) on 21 Aug 1999 |
| BFC Dynamo beat Dynamo Dresden 1-0 (H) on 7 Sep 1999 |
FLP: Thick arrows show the earliest chain of wins that passes through every team.