Daniel Stoehr defeated Kevin Deden 7-5 6-4 in the Germany F20 qualifying round on clay. The upset overturned the form book — Kevin Deden came in leading the head-to-head 2–1. Daniel Stoehr narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-09-29 | Germany F21 | R32 | carpet | Kevin Deden | 6-4 6-3 |
| 2008-07-07 | Germany F10 | R32 | clay | Kevin Deden | 6-3 6-3 |
| 2006-10-02 | Germany 1 Satellite 2 | QF | carpet | Daniel Stoehr | 7-6(4) 6-2 |