Evthimios Karaliolios defeated Romano Frantzen 6-2 4-6 6-2 in the Netherlands F4 round of 32 on clay. The upset overturned the form book — Romano Frantzen came in leading the head-to-head 1–0. Evthimios Karaliolios claimed a first win over Romano Frantzen in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-22 | Netherlands F3 | R16 | clay | Romano Frantzen | 3-6 6-3 6-4 |