Romano Frantzen defeated Evthimios Karaliolios 3-6 6-3 6-4 in the Netherlands F3 round of 16 on clay. The upset overturned the form book — Evthimios Karaliolios came in leading the head-to-head 1–0, but Romano Frantzen had been the form player, winning 2 of their last 6 on clay. Romano Frantzen claimed a first win over Evthimios Karaliolios in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-08-18 | Netherlands F4 | R32 | clay | Evthimios Karaliolios | 6-2 4-6 6-2 |