Yordan Kanev defeated Tihomir Grozdanov 4-6 6-2 6-2 in the Bulgaria 1 4 round of 32 on clay. The upset overturned the form book — Tihomir Grozdanov came in leading the head-to-head 2–0. Yordan Kanev claimed a first win over Tihomir Grozdanov in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-05-12 | Bulgaria F2 | R16 | clay | Tihomir Grozdanov | 6-2 6-1 |
| 2007-08-20 | Bulgaria F5 | QF | clay | Tihomir Grozdanov | 2-6 6-1 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.