| H5 | | Fr | 19.09.08 | | 20:00 | Rödemisser SV | TSV Oldenswort II | 7:7 | |
| H8 | | Fr | 26.09.08 | | 20:00 | TSV Oldenswort II | TTC Högel IV | 6:8 | |
| H11 | | Do | 02.10.08 | | 20:00 | TTC Högel V | TSV Oldenswort II | 7:7 | |
| H17 | | Mo | 27.10.08 | | 20:30 | TSV Osten-Witt-Winn | TSV Oldenswort II | 7:7 | |
| H24 | | Fr | 07.11.08 | | 20:00 | TSV Oldenswort II | TTG Sylt-Ost III | 6:8 | |
| H28 | | Fr | 14.11.08 | | 19:30 | Husumer SV seit 1875 III | TSV Oldenswort II | 3:8 | |
| H34 | | Fr | 21.11.08 | | 20:00 | TSV Oldenswort II | TSV Stedesand II | 8:3 | |
| H36 | | Di | 25.11.08 | | 20:00 | TSV Nordstrand 03 III | TSV Oldenswort II | 8:5 | |
| H44 | | Fr | 05.12.08 | | 20:00 | TSV Oldenswort II | TTV Koldenbüttel IV | 8:5 | |
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