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 | 2016/11/20 08:00 | Michalis Sakellaridis v Martin Atanasov | 6-2,6-2 |
| ITF Greece F10 Qual | 2016/11/12 07:00 | Martin Atanasov v Aljaz Jakob Kaplja | 2-6,0-6 |
| ITF Spain F10 Qual | 2016/04/16 12:00 | Martin Atanasov v Diego-Jose Manrique-Velazquez | 1-6,2-6 |
| ITF Bulgaria F1 Qual | 2015/06/07 07:00 | Gabriel Donev v Martin Atanasov | 6-2,6-2 |