Ivaylo Traykov defeated Tihomir Grozdanov 6-1 6-4 in the Bulgaria F2 qualifying round on clay. The upset overturned the form book — Tihomir Grozdanov came in leading the head-to-head 5–4. Ivaylo Traykov narrowed the head-to-head to 5–5.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-05-17 | Bulgaria F3 | R32 | clay | Tihomir Grozdanov | 7-6(6) 6-2 |
| 2009-05-04 | Bulgaria F1 | F | clay | Ivaylo Traykov | 2-6 6-4 6-3 |
| 2008-09-08 | Bulgaria F8 | F | clay | Tihomir Grozdanov | 7-5 1-0 |
| 2008-05-05 | Bulgaria F1 | R16 | clay | Ivaylo Traykov | 6-3 6-4 |
| 2007-08-27 | Bulgaria F6 | R32 | clay | Tihomir Grozdanov | 7-5 3-6 7-6(0) |
| 2007-08-20 | Bulgaria F5 | R16 | clay | Tihomir Grozdanov | 6-7(4) 7-6(3) 6-3 |
| 2006-09-04 | Bulgaria F3 | R16 | clay | Ivaylo Traykov | 4-6 6-4 6-4 |
| 2006-08-28 | Bulgaria F2 | R16 | clay | Ivaylo Traykov | 6-3 4-6 6-4 |
| 2005-05-02 | Bulgaria 1 2 | R16 | clay | Tihomir Grozdanov | 6-3 3-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.