Round: 44 Ground: Hardcourt outdoor
| ITF Bulgaria F1 | 2016/05/20 08:00 | Tihomir Grozdanov v Alexander Lazov | 3-6,1-6 |
| ITF Bulgaria F1 | 2016/05/19 09:15 | Tihomir Grozdanov v Aria Harajchi | 6-4,6-2 |
| ITF Bulgaria F1 | 2016/05/18 10:05 | Anton Pavlov v Tihomir Grozdanov | 6-2,4-6,0-6 |
| ITF Bosnia and Herzegovina F1 | 2016/05/10 14:55 | Gorazd Srbljak v Tihomir Grozdanov | 6-3,6-0 |
| ITF Bosnia and Herzegovina F1 Qual | 2016/05/09 08:00 | Tihomir Grozdanov v Shinnosuke Hiramatsu | 6-2,6-1 |
| Davis Cup | 2015/07/19 10:30 | Alex Knaff v Tihomir Grozdanov | 3-6,7-5,4-6 |
| ITF Bulgaria F1 | 2015/06/11 07:00 | Petru-Alexandru Luncanu v Tihomir Grozdanov | 6-2,6-3 |
| ITF Bulgaria F1 | 2015/06/10 07:00 | Cosmin Ontica v Tihomir Grozdanov | 0-6,2-6 |
| ITF Greece F11 | 2016/11/19 07:30 | Lazar Dokov v Stephanos Schinas | 0-6,3-6 |
| ITF Greece F10 Qual | 2016/11/12 07:00 | Lazar Dokov v Stefan Petrovic | 0-6,1-6 |
| ITF Greece F9 Qual | 2016/11/05 07:30 | Lazar Dokov v Antoine Walch | 1-6,2-6 |
| ITF Serbia F5 Qual | 2016/08/14 10:00 | Antun Vidak v Lazar Dokov | 6-1,6-2 |
| ITF Turkey F31 | 2015/06/27 10:00 | Lazar Dokov v Odil Akramov | 1-6,1-6 |
| ITF Bulgaria F1 Qual | 2015/06/06 09:00 | Ethan Tulliani v Lazar Dokov | 3-6,4-6 |