| UTR Pro Tennis Series Copenhagen | 2022/04/26 06:00 | Plamen Milushev v Marcelo Zormann | 4-6,6-6 |
| UTR Pro Tennis Series Copenhagen | 2022/04/25 10:55 | Plamen Milushev v Christian Heaney-Secord | 1-6,3-6 |
| UTR Pro Tennis Series Barcelona | 2022/03/31 14:08 | Ivan Penev v Plamen Milushev | 6-2,1-0 |
| UTR Pro Tennis Series Barcelona | 2022/03/30 09:30 | Quentin Robert v Plamen Milushev | 6-2,6-2 |
| UTR Pro Tennis Series Barcelona | 2022/03/29 12:00 | Vladimir Popov v Plamen Milushev | 3-6,1-6 |
| UTR Pro Tennis Series Barcelona | 2022/03/28 09:00 | Gabriel Donev v Plamen Milushev | 5-7,6-3,6-1 |
| 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 |
| UTR Pro Tennis Series Copenhagen | 2022/04/26 06:00 | Christian Heaney-Secord v Simon A Ivanov | 4-6,6-1,3-6 |
| ITF M15 Dubrovnik | 2022/04/06 12:55 | Simon A Ivanov v Andrea Guerrieri | 3-6,5-7 |
| UTR Pro Tennis Series Barcelona | 2022/03/31 14:08 | Simon A Ivanov v David Jorda Sanchis | 6-2,3-6,1-6 |
| UTR Pro Tennis Series Barcelona | 2022/03/30 15:00 | Simon A Ivanov v Adria Soriano Barrera | 4-6,3-6 |
| UTR Pro Tennis Series Barcelona | 2022/03/29 11:29 | Simon A Ivanov v Jaume Pla Malfeito | 7-5,6-3 |
| UTR Pro Tennis Series Barcelona | 2022/03/28 09:09 | Simon A Ivanov v Mario M Martin | 3-6,1-6 |
| ITF M25 Antalya | 2022/03/08 10:55 | Simon A Ivanov v Felix Gill | 2-6,2-6 |
| ITF M15 Antalya | 2022/03/04 08:05 | Simon A Ivanov v Alex M Pujolras | 3-6,2-6 |