Round: 44 Ground: Clay
| ITF - M15 Antalya | 2019/11/17 06:30 | Donmezer, Enes v Radosavljevic, Mihailo | 4-6,4-6 |
| Burgas, Singles Qualifying M-ITF-BUL-05A | 2019/10/06 08:00 | Dian Nedev v Radosavljevic, Mihailo | 6-4,6-2 |
| 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 |
| ITF - M15 Antalya | 2019/11/17 06:30 | Rudiukov, Ilya v Filip, Vladimir | 5-7,5-7 |
| ITF - M15 Antalya | 2019/11/11 10:45 | Tomas Farjat v Filip, Vladimir | 6-3,6-0 |
| ITF - M15 Antalya | 2019/11/11 06:30 | Michalis Sakellaridis v Filip, Vladimir | 6-3,5-7,5-10 |
| ITF - M15 Antalya | 2019/11/10 08:30 | Yehayan, Mikhail v Filip, Vladimir | 4-6,6-7 |
| Burgas, Singles Qualifying M-ITF-BUL-05A | 2019/10/09 12:55 | Ivanov, Simon Anthony v Filip, Vladimir | 1-6,6-2,6-3 |
| Burgas, Singles Qualifying M-ITF-BUL-05A | 2019/10/08 12:00 | Michael Gloeckler v Filip, Vladimir | 6-0,6-2 |
| Burgas, Singles Qualifying M-ITF-BUL-05A | 2019/10/07 11:00 | Iliev, Martin v Filip, Vladimir | 2-6,2-6 |
| Burgas, Singles Qualifying M-ITF-BUL-05A | 2019/10/07 07:00 | Basriev, Tolga v Filip, Vladimir | 0-6,2-6 |