Round: 25 Ground: Clay
| ITF Bulgaria F1 | 2014/06/12 07:00 | Dimitar Kuzmanov v Milushev, Plamen | 7-6,6-3 |
| Turkey F25, Singles Qualifying | 2017/07/10 07:00 | Valentin Vanta v Milushev, Plamen | 5-7,6-7 |
| Turkey F25, Singles Qualifying | 2017/07/09 07:00 | Milushev, Plamen v Darrshan Suresh | 6-2,6-2 |
| Turkey F25, Singles Qualifying | 2017/07/08 09:00 | Vicentiu Andrei Niculescu v Milushev, Plamen | 1-6,1-6 |
| ITF Indonesia F5 | 2015/12/12 07:30 | Bogaert, Dennis v Milushev, Plamen | 6-4,6-2 |
| ITF Serbia F8 | 2015/08/19 08:00 | Bortolotti, Marco v Milushev, Plamen | 6-1,6-1 |
| ITF Serbia F8 | 2015/08/13 11:20 | Raspudic, Franjo v Milushev, Plamen | 6-1,1-6,6-2 |
| ITF Serbia F8 | 2015/08/11 09:35 | Milushev, Plamen v Reboul, Fabien | 4-6,6-4,6-3 |
| ITF Serbia F8 Qual | 2015/08/10 08:00 | Milushev, Plamen v Mayer, Patrick | 6-2,7-5 |
| ITF Turkey F24 | 2017/06/25 08:00 | Sieber, Marc v Dimitar Kuzmanov | 3-6,6-2,1-6 |
| ITF Turkey F24 | 2017/06/24 07:00 | Dimitar Kuzmanov v Vilella Martinez, Mario | 6-7,6-4,6-3 |
| ITF Turkey F24 | 2017/06/23 08:40 | Kekez, Duje v Dimitar Kuzmanov | 3-6,2-6 |
| ITF Turkey F24 | 2017/06/22 07:00 | Cortes Alcaraz, Aaron v Dimitar Kuzmanov | 0-6,0-6 |
| ITF Turkey F24 | 2017/06/20 07:00 | Cengiz Aksu v Dimitar Kuzmanov | 0-6,3-6 |
| ITF Turkey F23 | 2017/06/16 09:35 | Nedelko, Ivan v Dimitar Kuzmanov | 6-3,7-5 |
| ITF Turkey F23 | 2017/06/15 07:00 | Dimitar Kuzmanov v Karim-Mohamed Maamoun | 6-3,6-4 |
| ITF Turkey F23 | 2017/06/14 08:35 | Sarp Agabigun v Dimitar Kuzmanov | 7-6,5-7,0-6 |