Stadium: Court 2 Round: 62 Ground: Clay
| ITF M15 Antalya | 2021/01/04 07:00 | Plamen Milushev v Aleksandr Lobanov | 6-3,6-2 |
| ITF M15 Plovdiv | 2019/06/04 10:30 | Riccardo Maiga v Plamen Milushev | 7-5,3-6,10-4 |
| ITF M15 Plovdiv | 2019/06/04 06:30 | Martin Dimitrov v Plamen Milushev | 6-0,5-7,9-11 |
| ITF M15 Sozopol | 2019/05/09 07:00 | Plamen Milushev v Vasil Kirkov | 2-6,3-6 |
| ITF M15 Sozopol | 2019/05/07 10:00 | Plamen Milushev v Dian Nedev | 6-2,6-2 |
| ITF Turkey F38 | 2018/11/25 07:00 | Bjorn Nareyka v Plamen Milushev | 0-6,6-7 |
| ITF Turkey F37 | 2018/11/22 08:10 | Dejan Katic v Plamen Milushev | 4-6,6-4,6-3 |
| ITF Turkey F37 | 2018/11/21 07:00 | Plamen Milushev v Samuel Pointon | 6-0,6-3 |
| ITF M15 Antalya | 2020/12/20 07:00 | Suleyman Deniz Gursoy v Nikita Naskidashvili | 3-6,0-6 |
| ITF M15 Antalya | 2020/12/15 11:00 | Suleyman Deniz Gursoy v Daniil Savelev | 3-6,3-6 |
| ITF M15 Antalya | 2020/12/06 07:00 | Dragos Nicolae Madaras v Suleyman Deniz Gursoy | 6-1,6-2 |
| ITF M15 Antalya | 2020/11/30 12:30 | Suleyman Deniz Gursoy v Martin Dimitrov | 1-6,0-6 |
| ITF M15 Antalya | 2020/11/29 06:00 | Klim Kozyrev v Suleyman Deniz Gursoy | 4-6,4-6 |