Tihomir Grozdanov defeated Valentin Dimov 6-1 6-1 in the Bulgaria F5 round of 32 on clay. The result followed the form book — Tihomir Grozdanov came in leading the head-to-head 7–1. Tihomir Grozdanov extended the head-to-head to 8–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2014-06-30 | Bulgaria F4 | R32 | clay | Tihomir Grozdanov | 6-3 6-3 |
| 2012-02-20 | Turkey F7 | R16 | hard | Tihomir Grozdanov | 7-6(5) 6-1 |
| 2011-08-22 | Serbia F8 | R32 | clay | Valentin Dimov | 3-6 7-5 6-0 |
| 2008-08-25 | Bulgaria F6 | R32 | clay | Tihomir Grozdanov | 6-1 6-3 |
| 2008-08-18 | Bulgaria F5 | R32 | clay | Tihomir Grozdanov | 6-3 6-3 |
| 2008-05-05 | Bulgaria F1 | R32 | clay | Tihomir Grozdanov | 6-1 6-4 |
| 2007-08-20 | Bulgaria F5 | R32 | clay | Tihomir Grozdanov | 6-2 6-4 |
| 2006-08-21 | Bulgaria F1 | R32 | clay | Tihomir Grozdanov | 6-3 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.