Valentin Dimov defeated Arthur De Greef 6-3 5-7 6-0 in the Belgium F3 round of 16 on clay. The upset overturned the form book — Arthur De Greef came in leading the head-to-head 1–0, but Valentin Dimov had been the form player, winning 6 of their last 9 on clay. Valentin Dimov claimed a first win over Arthur De Greef in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-09-28 | Greece F2 | R16 | carpet | Arthur De Greef | 7-5 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.