Stadium: Court 8 ParkEzeroto Round: 44 Ground: Clay
| ITF M15 Burgas | 2019/10/06 08:00 | Benjamin Niv v Valentin Ivanov | 7-5,6-3 |
| ITF M15 Chornomorsk | 2019/09/24 08:05 | Marco Bortolotti v Benjamin Niv | 3-6,6-0,6-3 |
| ITF M15 Varna | 2019/09/12 07:00 | Quentin Folliot v Benjamin Niv | 6-1,6-1 |
| ITF M15 Varna | 2019/09/11 10:00 | Benjamin Niv v Yannick Lenaerts | 6-2,6-3 |
| ITF M15 Varna | 2019/09/09 13:00 | Benjamin Niv v Nir Vodavoz | 3-6,3-6 |
| ITF M15 Varna | 2019/09/09 06:30 | Benjamin Niv v Radoslav Shandarov | 3-6,7-6,15-13 |
| ITF M25 Dublin | 2019/07/29 13:00 | Benjamin Niv v Philip Lynch | 4-6,3-6 |
| ITF M15 Plovdiv | 2019/06/04 06:30 | Alexander Weis v Benjamin Niv | 6-4,6-4 |
| ITF M15 Burgas | 2019/10/06 08:00 | Dian Nedev v Mihailo Radosavljevic | 6-4,6-2 |
| ITF M15 Varna | 2019/09/10 08:00 | Juan Pablo Paz v Dian Nedev | 6-2,7-6 |
| ITF M15 Plovdiv | 2019/06/04 08:30 | Gorazd Srbljak v Dian Nedev | 7-6,6-0 |
| ITF M15 Plovdiv | 2019/06/03 10:00 | Dian Nedev v Vladimir Filip | 7-6,6-0 |
| ITF M15 Sozopol | 2019/05/07 10:00 | Plamen Milushev v Dian Nedev | 6-2,6-2 |
| ITF Greece F8 | 2018/11/10 07:30 | Dian Nedev v George Davies | 6-7,2-6 |
| ITF Greece F7 | 2018/11/03 10:00 | Alexandros Roumpis v Dian Nedev | 6-1,6-2 |
| ITF Germany F7 | 2017/07/09 08:00 | Mark Burgos v Dian Nedev | 6-4,6-1 |