Round: 44 Ground: Clay
| Varna, Singles M-ITF-BUL-04A | 2019/09/10 08:00 | Juan Pablo Paz v Dian Nedev | 6-2,7-6 |
| Plovdiv, Singles Qualifying M-ITF-BUL-03A | 2019/06/04 08:30 | Gorazd Srbljak v Dian Nedev | 7-6,6-0 |
| Plovdiv, Singles Qualifying M-ITF-BUL-03A | 2019/06/03 10:00 | Dian Nedev v Filip, Vladimir | 7-6,6-0 |
| ITF M15 Sozopol | 2019/05/07 10:00 | Milushev, Plamen v Dian Nedev | 6-2,6-2 |
| ITF Greece F8 | 2018/11/10 07:30 | Dian Nedev v Davies, George | 6-7,2-6 |
| ITF Greece F7 | 2018/11/03 10:00 | Roumpis, Alexandros v Dian Nedev | 6-1,6-2 |
| ITF Germany F7 | 2017/07/09 08:00 | Burgos, Mark v Dian Nedev | 6-4,6-1 |
| ITF M15 Zlatibor | 2019/09/18 07:30 | Radosavljevic, Mihailo v Filip Misolic | 3-6,2-6 |
| ITF M15 Zlatibor | 2019/09/17 07:00 | Suntic, Sabit v Radosavljevic, Mihailo | 4-6,2-6 |
| ITF M15 Zlatibor | 2019/09/16 10:30 | Radosavljevic, Mihailo v Feler, Melik | 6-0,6-2 |
| ITF M15 Novi Sad | 2019/08/05 10:30 | Radosavljevic, Mihailo v Shendrit Deari | 3-6,6-7 |