Stadium: Court 5 Round: 44 Ground: Clay
| ITF M15 Plovdiv | 2019/06/04 06:30 | Martin Dimitrov v Plamen Milushev | 6-0,5-7,9-11 |
| UTR Pro Tennis Series Dobrich | 2022/02/27 07:23 | Petr Nesterov v Martin Dimitrov | 6-3,4-6,7-5 |
| UTR Pro Tennis Series Dobrich | 2022/02/26 09:29 | Martin Dimitrov v Gabriel Donev | 6-4,1-4 |
| UTR Pro Tennis Series Dobrich | 2022/02/25 09:00 | Ivan Penev v Martin Dimitrov | 7-5,6-1 |
| UTR Pro Tennis Series Dobrich | 2022/02/24 07:30 | George Lazarov v Martin Dimitrov | 5-7,6-2,6-7 |
| UTR Pro Tennis Series Dobrich | 2022/02/23 12:00 | Maciej Rajski v Martin Dimitrov | 6-4,6-2 |
| UTR Pro Tennis Series Dobrich | 2022/02/21 07:30 | Anthony Genov v Martin Dimitrov | 1-6,1-6 |
| UTR Pro Tennis Series Barcelona | 2021/12/16 09:00 | Sergio Redondo v Martin Dimitrov | 6-3,6-3 |
| UTR Pro Tennis Series Barcelona | 2021/12/15 13:00 | Pol Del Castillo v Martin Dimitrov | 3-6,6-2,5-4 |
| ITF M15 Sozopol | 2021/10/05 06:30 | Berk Ilkel v Plamen Milushev | 6-3,7-5 |
| ITF M15 Sozopol | 2021/10/04 08:00 | S Mert Ozdemir v Plamen Milushev | 2-6,6-3,5-10 |
| ITF M15 Sozopol | 2021/10/03 10:30 | Amit Cohen v Plamen Milushev | 4-6,3-6 |
| ITF M15 Sozopol | 2021/09/15 07:00 | Plamen Milushev v George Tsivadze | 4-6,3-6 |
| ITF M15 Sozopol | 2021/09/14 07:00 | Plamen Milushev v Samuil Konov | 6-4,6-3 |
| ITF M15 Sozopol | 2021/09/13 07:00 | Plamen Milushev v Nikola Kolyachev | 6-4,6-3 |
| UTR Pro Tennis Series Sofia | 2021/08/30 08:30 | Plamen Milushev v Dian Nedev | 4-6,2-5 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/18 09:00 | Yanaki Milev v Plamen Milushev | 3-6,6-6 |