| TeBe Berlin II beat Union Berlin 2-1 (A) on 21 Nov 1999 |
| Union Berlin beat BFC Dynamo 3-0 (A) on 23 Oct 1999 |
| BFC Dynamo beat Dynamo Dresden 1-0 (H) on 7 Sep 1999 |
| Dynamo Dresden beat FSV Zwickau 1-0 (H) on 16 Oct 1999 |
| FSV Zwickau beat Sachsen Leipzig 3-1 (H) on 23 Oct 1999 |
| Sachsen Leipzig beat VFC Plauen 2-1 (H) on 11 Aug 1999 |
| VFC Plauen beat Dresdner 3-1 (H) on 26 Sep 1999 |
| Dresdner beat Carl Zeiss Jena 2-1 (H) on 23 Oct 1999 |
| Carl Zeiss Jena beat Erzgebirge Aue 2-1 (A) on 11 Sep 1999 |
| Erzgebirge Aue beat VfL Halle 96 3-1 (A) on 11 Aug 1999 |
| VfL Halle 96 beat Hertha BSC II 1-0 (A) on 24 Oct 1999 |
| Hertha BSC II beat Stahl Eisenhüttenstadt 1-0 (H) on 21 Aug 1999 |
| Stahl Eisenhüttenstadt beat Rot Weiß Erfurt 2-0 (H) on 14 Aug 1999 |
| Rot Weiß Erfurt beat Magdeburg 1-0 (H) on 11 Sep 1999 |
| Magdeburg beat Lok Altmark Stendal 4-1 (A) on 7 Nov 1999 |
| Lok Altmark Stendal beat SV Babelsberg 03 1-0 (H) on 25 Aug 1999 |
| SV Babelsberg 03 beat VfB Leipzig 3-1 (H) on 11 Aug 1999 |
| VfB Leipzig beat TeBe Berlin II 2-0 (H) on 14 Aug 1999 |
HWC: Thick arrows show the earliest chain of wins that passes through every team and returns to its start.