| UTR Pro Tennis Series Copenhagen | 2022/04/26 06:00 | Milushev, Plamen v Marcelo Zormann | 4-6,6-6 |
| UTR Pro Tennis Series Copenhagen | 2022/04/25 10:55 | Milushev, Plamen v Christian Heaney-Secord | 1-6,3-6 |
| UTR Pro Tennis Series Barcelona | 2022/03/31 14:08 | Penev, Ivan v Milushev, Plamen | 6-2,1-0 |
| UTR Pro Tennis Series Barcelona | 2022/03/30 09:30 | Robert, Quentin v Milushev, Plamen | 6-2,6-2 |
| UTR Pro Tennis Series Barcelona | 2022/03/29 12:00 | Vladimir Popov v Milushev, Plamen | 3-6,1-6 |
| UTR Pro Tennis Series Barcelona | 2022/03/28 09:00 | Gabriel Donev v Milushev, Plamen | 5-7,6-3,6-1 |
| ITF M15 Sozopol | 2021/10/05 06:30 | Berk Ilkel v Milushev, Plamen | 6-3,7-5 |
| ITF M15 Sozopol | 2021/10/04 08:00 | S Mert Ozdemir v Milushev, Plamen | 2-6,6-3,5-10 |
| UTR Pro Tennis Series Copenhagen | 2022/04/26 06:00 | Christian Heaney-Secord v Ivanov, Simon Anthony | 4-6,6-1,3-6 |
| ITF - M15 Dubrovnik | 2022/04/06 12:55 | Ivanov, Simon Anthony v Andrea Guerrieri | 3-6,5-7 |
| UTR Pro Tennis Series Barcelona | 2022/03/31 14:08 | Ivanov, Simon Anthony v David Jorda Sanchis | 6-2,3-6,1-6 |
| UTR Pro Tennis Series Barcelona | 2022/03/30 15:00 | Ivanov, Simon Anthony v Adria Soriano Barrera | 4-6,3-6 |
| UTR Pro Tennis Series Barcelona | 2022/03/29 11:29 | Ivanov, Simon Anthony v Pla Malfeito, Jaume | 7-5,6-3 |
| UTR Pro Tennis Series Barcelona | 2022/03/28 09:09 | Ivanov, Simon Anthony v Mario M Martin | 3-6,1-6 |
| ITF - M25 Antalya | 2022/03/08 10:55 | Ivanov, Simon Anthony v Felix Gill | 2-6,2-6 |
| ITF - M15 Antalya | 2022/03/04 08:05 | Ivanov, Simon Anthony v Alex M Pujolras | 3-6,2-6 |