Stadium: Court 1 Round: 44 Ground: Clay
| ITF M15 Antalya | 2021/01/07 08:40 | Plamen Milushev v Alexander Shevchenko | 1-6,5-7 |
| ITF M15 Antalya | 2021/01/06 07:30 | Plamen Milushev v Suleyman Deniz Gursoy | 6-0,6-2 |
| 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 M15 Kazan | 2021/03/08 07:00 | Daniel Ibragimov v Leonid Sheyngezikht | 4-6,6-4,10-8 |
| ITF M15 St Petersburg Qual | 2021/02/07 10:00 | Alexander Cozbinov v Leonid Sheyngezikht | 6-4,6-3 |
| ITF M15 St Petersburg | 2021/02/01 07:00 | Daniil Glinka v Leonid Sheyngezikht | 6-3,6-4 |
| ITF M15 St Petersburg | 2021/01/31 10:10 | Leonid Sheyngezikht v A.J Catanzariti | 6-2,6-2 |
| ITF M15 Cairo | 2020/12/08 09:00 | Ivan Denisov v Leonid Sheyngezikht | 3-6,6-2,10-7 |
| ITF M15 Cairo | 2020/12/06 12:00 | Arjun Mahadevan v Leonid Sheyngezikht | 0-6,1-6 |
| ITF M15 Cairo | 2020/11/30 11:30 | Juan Bautista Otegui v Leonid Sheyngezikht | 6-3,6-2 |
| ITF M15 Cairo | 2020/11/29 13:00 | Leonid Sheyngezikht v Belal Abou Taleb | 7-5,6-4 |