| ITF Turkey F32 | 2018/10/15 07:00 | Gabriel Donev v Milushev, Plamen | 6-4,6-3 |
| ITF Bulgaria F1 | 2014/06/10 07:00 | Gabriel Donev v Milushev, Plamen | 4-6,7-5,5-7 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/06 08:30 | Gabriel Donev v Yanaki Milev | 6-2,5-1 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/05 13:00 | de La Bassetiere, Constant v Gabriel Donev | 5-7,1-6 |
| ITF - M15 Antalya | 2021/03/30 07:00 | Gabriel Donev v Diego A B Sanchez | 4-6,6-1,7-10 |
| ITF - M15 Antalya | 2021/03/29 07:00 | Gabriel Donev v Stefanos Sakellaridis | 6-3,5-7,10-2 |
| ITF - M15 Antalya | 2021/03/28 06:30 | Gabriel Donev v Mikail Alimli | 6-1,6-2 |
| ITF - M15 Antalya | 2021/03/24 06:30 | Gabriel Donev v Max Alcala Gurri | 1-6,1-6 |
| ITF - M15 Antalya | 2021/03/22 07:00 | Gabriel Donev v Bautista Vilicich | 6-1,6-3 |
| ITF - M15 Antalya | 2021/03/21 07:00 | Gabriel Donev v Rafael Giotis | 7-5,6-0 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/05 13:00 | Joncour, Ronan v Milushev, Plamen | 6-1,6-3 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/01 10:00 | Anthony Genov v Milushev, Plamen | 6-3,4-2 |
| UTR Pro Tennis Series Pazardzhik | 2021/03/31 10:00 | Aristotelis Thanos v Milushev, Plamen | 7-5,5-2 |
| UTR Pro Tennis Series Pazardzhik | 2021/03/29 11:00 | Lucas Bouquet v Milushev, Plamen | 6-3,5-0 |
| ITF - M15 Antalya | 2021/01/07 08:40 | Milushev, Plamen v Alexander Shevchenko | 1-6,5-7 |
| ITF - M15 Antalya | 2021/01/06 07:30 | Milushev, Plamen v Suleyman Deniz Gursoy | 6-0,6-2 |
| ITF - M15 Antalya | 2021/01/04 07:00 | Milushev, Plamen v Aleksandr Lobanov | 6-3,6-2 |
| Plovdiv, Singles Qualifying M-ITF-BUL-03A | 2019/06/04 10:30 | Maiga, Riccardo v Milushev, Plamen | 7-5,3-6,10-4 |