Tihomir Grozdanov defeated Yordan Kanev 2-6 6-1 6-3 in the Bulgaria F5 qualifying round on clay. Tihomir Grozdanov extended 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 |
| 2006-05-01 | Bulgaria 1 4 | R32 | clay | Yordan Kanev | 4-6 6-2 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.