Ralph Grambow defeated Frank Wintermantel 6-3 6-2 in the Germany F4 round of 32 on carpet. The upset overturned the form book — Frank Wintermantel came in leading the head-to-head 1–0. Ralph Grambow claimed a first win over Frank Wintermantel in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-06-16 | Norway F2 | R32 | hard | Frank Wintermantel | 6-2 6-2 |