Romano Frantzen defeated Matwe Middelkoop 7-5 6-3 in the Netherlands F4 round of 32 on clay. The upset overturned the form book — Matwe Middelkoop came in leading the head-to-head 1–0. Romano Frantzen claimed a first win over Matwe Middelkoop in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-08-27 | Netherlands F5 | R16 | clay | Matwe Middelkoop | 7-5 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.