| H1 | | Fr | 12.09.08 | | 20:00 | TTG Sylt-Ost III | TTV Koldenbüttel IV | 6:8 | |
| H13 | | Fr | 10.10.08 | | 20:00 | Rödemisser SV | TTG Sylt-Ost III | 8:1 | |
| H15 | | So | 26.10.08 | v | 12:30 | TSV Osten-Witt-Winn | TTG Sylt-Ost III | 8:3 | |
| H16 | | So | 26.10.08 | | 15:30 | TSV Nordstrand 03 III | TTG Sylt-Ost III | 8:4 | |
| H19 | | Fr | 31.10.08 | | 20:00 | TTG Sylt-Ost III | TTC Högel IV | 7:7 | |
| H24 | | Fr | 07.11.08 | | 20:00 | TSV Oldenswort II | TTG Sylt-Ost III | 6:8 | |
| H33 | | Fr | 21.11.08 | | 20:00 | TTG Sylt-Ost III | TTC Högel V | 8:5 | |
| H38 | | Fr | 28.11.08 | | 19:30 | Husumer SV seit 1875 III | TTG Sylt-Ost III | 7:7 | |
| H43 | | Fr | 05.12.08 | | 20:00 | TTG Sylt-Ost III | TSV Stedesand II | 8:3 | |
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