| | Liga | Jahr | | Spieltag | Datum | | Heim | Gast | Ergebnis |
| | Landesliga Westfalen 1 | 1999-2000 | | 1 | 08.08.1999 | | FC Gütersloh II | SV Gadderbaum | 3 | 0 |
| | Landesliga Westfalen 1 | 1999-2000 | | 2 | 15.08.1999 | | SV Gadderbaum | SV Avenwedde | 2 | 1 |
| | Landesliga Westfalen 1 | 1999-2000 | | 3 | 22.08.1999 | | SC Rot-Weiß Maaslingen | SV Gadderbaum | 5 | 3 |
| | Landesliga Westfalen 1 | 1999-2000 | | 4 | 29.08.1999 | | SV Gadderbaum | SV Werl-Aspe | 7 | 1 |
| | Landesliga Westfalen 1 | 1999-2000 | | 5 | 05.09.1999 | | TBV Lemgo | SV Gadderbaum | 0 | 1 |
| | Landesliga Westfalen 1 | 1999-2000 | | 6 | 12.09.1999 | | SV Gadderbaum | SuS Vlotho-Winterberg | 3 | 2 |
| | Landesliga Westfalen 1 | 1999-2000 | | 7 | 19.09.1999 | | TuS Horn-Bad Meinberg | SV Gadderbaum | 1 | 1 |
| | Landesliga Westfalen 1 | 1999-2000 | | 8 | 26.09.1999 | | SV Gadderbaum | TuS Petershagen-Ovenstädt | 2 | 3 |
| | Landesliga Westfalen 1 | 1999-2000 | | 9 | 03.10.1999 | | TuS Jöllenbeck | SV Gadderbaum | 1 | 1 |
| | Landesliga Westfalen 1 | 1999-2000 | | 10 | 10.10.1999 | | SV Gadderbaum | VfB Fichte Bielefeld II | 2 | 1 |
| | Landesliga Westfalen 1 | 1999-2000 | | 11 | 17.10.1999 | | DSC Arminia Bielefeld II | SV Gadderbaum | 8 | 1 |
| | Landesliga Westfalen 1 | 1999-2000 | | 12 | 24.10.1999 | | SV Gadderbaum | SV Höxter | 2 | 2 |
| | Landesliga Westfalen 1 | 1999-2000 | | 13 | 31.10.1999 | | VfB Schloß Holte | SV Gadderbaum | 1 | 0 |
| | Landesliga Westfalen 1 | 1999-2000 | | 14 | 07.11.1999 | | BV Bad Lippspringe | SV Gadderbaum | 3 | 1 |
| | Landesliga Westfalen 1 | 1999-2000 | | 15 | 14.11.1999 | | SV Gadderbaum | Union Minden | 2 | 0 |
| | Landesliga Westfalen 1 | 1999-2000 | | 16 | 28.11.1999 | | SV Gadderbaum | FC Gütersloh II | 3 | 3 |
| | Landesliga Westfalen 1 | 1999-2000 | | 17 | 05.12.1999 | | SV Avenwedde | SV Gadderbaum | 4 | 1 |
| | Landesliga Westfalen 1 | 1999-2000 | | 18 | 05.04.2000 | | SV Gadderbaum | SC Rot-Weiß Maaslingen | 3 | 3 |
| | Landesliga Westfalen 1 | 1999-2000 | | 19 | 12.03.2000 | | SV Werl-Aspe | SV Gadderbaum | 2 | 1 |
| | Landesliga Westfalen 1 | 1999-2000 | | 20 | 19.03.2000 | | SV Gadderbaum | TBV Lemgo | 1 | 1 |
| | Landesliga Westfalen 1 | 1999-2000 | | 21 | 20.04.2000 | | SuS Vlotho-Winterberg | SV Gadderbaum | 1 | 0 |
| | Landesliga Westfalen 1 | 1999-2000 | | 22 | 02.04.2000 | | SV Gadderbaum | TuS Horn-Bad Meinberg | 4 | 2 |
| | Landesliga Westfalen 1 | 1999-2000 | | 23 | 09.04.2000 | | TuS Petershagen-Ovenstädt | SV Gadderbaum | 0 | 1 |
| | Landesliga Westfalen 1 | 1999-2000 | | 24 | 14.04.2000 | | SV Gadderbaum | TuS Jöllenbeck | 3 | 5 |
| | Landesliga Westfalen 1 | 1999-2000 | | 25 | 12.04.2000 | | VfB Fichte Bielefeld II | SV Gadderbaum | 0 | 0 |
| | Landesliga Westfalen 1 | 1999-2000 | | 26 | 30.04.2000 | | SV Gadderbaum | DSC Arminia Bielefeld II | 0 | 1 |
| | Landesliga Westfalen 1 | 1999-2000 | | 27 | 07.05.2000 | | SV Höxter | SV Gadderbaum | 0 | 7 |
| | Landesliga Westfalen 1 | 1999-2000 | | 28 | 12.05.2000 | | SV Gadderbaum | VfB Schloß Holte | 0 | 3 |
| | Landesliga Westfalen 1 | 1999-2000 | | 29 | 21.05.2000 | | SV Gadderbaum | BV Bad Lippspringe | 3 | 0 |
| | Landesliga Westfalen 1 | 1999-2000 | | 30 | 28.05.2000 | | Union Minden | SV Gadderbaum | 2 | 1 |
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