Frank Wintermantel defeated Ralph Grambow 6-2 6-2 in the Norway F2 round of 32 on hard. The upset overturned the form book — Ralph Grambow came in leading the head-to-head 1–0. Frank Wintermantel claimed a first win over Ralph Grambow in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-01-23 | Germany F4 | R32 | carpet | Ralph Grambow | 6-3 6-2 |