| Hamburger SV II beat Holstein Kiel 1-0 (H) on 13 Nov 1999 |
| Holstein Kiel beat Bremerhaven 5-2 (A) on 31 Oct 1999 |
| Bremerhaven beat Eintracht Braunschweig 2-1 (A) on 1 Sep 1999 |
| Eintracht Braunschweig beat VfB Oldenburg 3-1 (A) on 23 Oct 1999 |
| VfB Oldenburg beat TuS Celle 3-1 (A) on 17 Oct 1999 |
| TuS Celle beat Arminia Hannover 3-1 (A) on 1 Aug 1999 |
| Arminia Hannover beat Werder Bremen II 2-1 (A) on 9 Oct 1999 |
| Werder Bremen II beat SC Göttingen 05 3-1 (A) on 16 Oct 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 BV Cloppenburg 2-0 (H) on 31 Oct 1999 |
| BV Cloppenburg beat St Pauli II 3-0 (H) on 26 Sep 1999 |
| St Pauli II beat VfB Lübeck 3-1 (H) on 3 Oct 1999 |
| VfB Lübeck beat Eintracht Nordhorn 4-2 (H) on 26 Sep 1999 |
| Eintracht Nordhorn beat SV Meppen 3-1 (H) on 10 Aug 1999 |
| SV Meppen beat SV Wilhelmshaven 2-1 (H) on 30 Jul 1999 |
| SV Wilhelmshaven beat SC Norderstedt 2-1 (A) on 15 Aug 1999 |
| SC Norderstedt beat Hamburger SV II 3-1 (H) on 31 Oct 1999 |
HWC: Thick arrows show the earliest chain of wins that passes through every team and returns to its start.