Matwe Middelkoop defeated Romano Frantzen 7-5 6-3 in the Netherlands F5 round of 16 on clay. The upset overturned the form book — Romano Frantzen came in leading the head-to-head 1–0. Matwe Middelkoop claimed a first win over Romano Frantzen in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-08-21 | Netherlands F4 | R32 | clay | Romano Frantzen | 7-5 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.