| Holstein Kiel beat St Pauli II 3-1 (H) on 10 Sep 1999 |
| St Pauli II beat SC Norderstedt 2-1 (A) on 28 Aug 1999 |
| SC Norderstedt beat VfB Lübeck 3-2 (H) on 31 Jul 1999 |
| VfB Lübeck beat BV Cloppenburg 7-1 (A) on 28 Aug 1999 |
| BV Cloppenburg beat VfB Oldenburg 3-1 (A) on 5 Sep 1999 |
| VfB Oldenburg beat Bremerhaven 5-2 (A) on 1 Aug 1999 |
| Bremerhaven beat Eintracht Braunschweig 2-1 (A) on 1 Sep 1999 |
| Eintracht Braunschweig beat Arminia Hannover 2-0 (H) on 6 Aug 1999 |
| Arminia Hannover beat SC Göttingen 05 5-1 (H) on 21 Aug 1999 |
| SC Göttingen 05 beat Lüneburger SK 2-1 (A) on 29 Aug 1999 |
| Lüneburger SK beat VfL Osnabrück 3-1 (H) on 11 Sep 1999 |
| VfL Osnabrück beat TuS Celle 1-0 (H) on 13 Aug 1999 |
| TuS Celle beat SV Meppen 1-0 (H) on 20 Aug 1999 |
| SV Meppen beat SV Wilhelmshaven 2-1 (H) on 30 Jul 1999 |
| SV Wilhelmshaven beat Werder Bremen II 2-1 (H) on 3 Sep 1999 |
| Werder Bremen II beat Eintracht Nordhorn 2-1 (H) on 10 Sep 1999 |
| Eintracht Nordhorn beat Hamburger SV II 2-1 (A) on 27 Aug 1999 |
FLP: Thick arrows show the earliest chain of wins that passes through every team.