| ITF Bulgaria F1 | 06/11 08:30 | - | Plamen Milushev v Albert Alcaraz Ivorra | 0-6,2-6 | |
| ITF Bulgaria F1 | 06/10 08:10 | - | Plamen Milushev v Vasko Mladenov | 6-4,7-5 | |
| ITF Greece F9 Qual | 11/05 11:45 | - | Stefanos Tsitsipas v Plamen Milushev | 6-2,6-1 | |
| ITF Serbia F8 | 08/19 09:20 | - | Antun Vidak v Plamen Milushev | 6-2,6-3 | |
| ITF Bulgaria F1 | 06/12 07:00 | - | Dimitar Kuzmanov v Plamen Milushev | 7-6,6-3 | |
| ITF Bulgaria F1 | 06/10 07:00 | - | Gabriel Donev v Plamen Milushev | 4-6,7-5,5-7 |