| 06.08.1999 | 19:00 | FSV Zwickau | - | Stahl Eisenhüttenstadt | 4:0 (1:0) | |
| 07.08.1999 | 13:00 | Rot-Weiß Erfurt | - | 1. FC Union Berlin | 0:1 (0:1) | |
| 14:00 | Dynamo Dresden | - | Lok Altmark Stendal | 1:1 (0:0) | ||
| 14:00 | TeBe Berlin II | - | Dresdner SC | 1:4 (1:3) | ||
| 10.08.1999 | 18:00 | Hertha BSC II | - | FC Carl Zeiss Jena | 1:1 (1:1) | |
| 11.08.1999 | 18:00 | SV Babelsberg 03 | - | VfB Leipzig | 3:1 (0:0) | |
| 18:00 | Sachsen Leipzig | - | VFC Plauen | 2:1 (2:1) | ||
| 18:00 | VfL Halle 96 | - | Erzgebirge Aue | 1:3 (1:0) | ||
| 19:00 | 1. FC Magdeburg | - | BFC Dynamo | 1:1 (1:1) |
| » Tabelle | Heim | Auswärts | Hinrunde | Rückrunde | 1. Halbzeit | 2. Halbzeit |
| # | Mannschaft | Sp. | S. | U. | N. | Tore | Dif. | Pk. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
FSV Zwickau | 1 | 1 | 0 | 0 | 4:0 | 4 | 3 |
| 2 |
|
Dresdner SC | 1 | 1 | 0 | 0 | 4:1 | 3 | 3 |
| 3 |
|
Erzgebirge Aue | 1 | 1 | 0 | 0 | 3:1 | 2 | 3 |
|
|
SV Babelsberg 03 | 1 | 1 | 0 | 0 | 3:1 | 2 | 3 | |
| 5 |
|
Sachsen Leipzig | 1 | 1 | 0 | 0 | 2:1 | 1 | 3 |
| 6 |
|
1. FC Union Berlin | 1 | 1 | 0 | 0 | 1:0 | 1 | 3 |
| 7 |
|
1. FC Magdeburg | 1 | 0 | 1 | 0 | 1:1 | 0 | 1 |
|
|
BFC Dynamo | 1 | 0 | 1 | 0 | 1:1 | 0 | 1 | |
|
|
Dynamo Dresden | 1 | 0 | 1 | 0 | 1:1 | 0 | 1 | |
|
|
FC Carl Zeiss Jena | 1 | 0 | 1 | 0 | 1:1 | 0 | 1 | |
|
|
Hertha BSC II | 1 | 0 | 1 | 0 | 1:1 | 0 | 1 | |
|
|
Lok Altmark Stendal | 1 | 0 | 1 | 0 | 1:1 | 0 | 1 | |
| 13 |
|
VFC Plauen | 1 | 0 | 0 | 1 | 1:2 | -1 | 0 |
| 14 |
|
Rot-Weiß Erfurt | 1 | 0 | 0 | 1 | 0:1 | -1 | 0 |
| 15 |
|
VfB Leipzig | 1 | 0 | 0 | 1 | 1:3 | -2 | 0 |
|
|
VfL Halle 96 | 1 | 0 | 0 | 1 | 1:3 | -2 | 0 | |
| 17 |
|
TeBe Berlin II | 1 | 0 | 0 | 1 | 1:4 | -3 | 0 |
| 18 |
|
Stahl Eisenhüttenstadt | 1 | 0 | 0 | 1 | 0:4 | -4 | 0 |