Tihomir Grozdanov defeated Gilles De Sousa 5-7 7-6 6-0 in the Bulgaria F3 round of 16 on clay. The upset overturned the form book — Gilles De Sousa came in leading the head-to-head 1–0, but Tihomir Grozdanov had been the form player, winning 5 of their last 6 on clay. Tihomir Grozdanov claimed a first win over Gilles De Sousa in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-11-09 | Turkey F13 | R16 | clay | Gilles De Sousa | 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.