Tihomir Grozdanov defeated Todor Enev 6-3 4-6 6-2 in the Bulgaria F1 round of 32 on clay. The upset overturned the form book — Todor Enev came in leading the head-to-head 2–0, but Tihomir Grozdanov had been the form player, winning 5 of their last 6 on clay. Tihomir Grozdanov claimed a first win over Todor Enev in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-09-01 | Bulgaria F7 | QF | clay | Todor Enev | 6-4 6-2 |
| 2006-08-21 | Bulgaria F1 | QF | clay | Todor Enev | 6-1 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.