| UTR Pro Tennis Series Barcelona | 2022/03/31 09:30 | Ivan Penev v Jordi Mas De Ugarte | 3-6,4-5 |
| UTR Pro Tennis Series Barcelona | 2022/03/29 09:00 | Ivan Penev v Maxence Broville | 7-5,6-3 |
| UTR Pro Tennis Series Barcelona | 2022/03/28 07:30 | Ivan Penev v Hugo Pierre | 5-7,1-5 |
| UTR Pro Tennis Series Barcelona | 2022/03/27 15:30 | Ivan Penev v David Redondo | 2-6,6-4,2-1 |
| UTR Pro Tennis Series - Bucuresti | 2022/03/09 09:00 | Dragos N Cazacu v Ivan Penev | 6-2,6-2 |
| UTR Pro Tennis Series - Bucuresti | 2022/03/07 11:00 | Dragos Constantin Ignat v Ivan Penev | 6-4,7-6 |
| UTR Pro Tennis Series - Bucuresti | 2022/03/06 12:30 | Dan Alexandru Tomescu v Ivan Penev | 6-2,5-1 |
| UTR Pro Tennis Series - Bucuresti | 2022/03/06 08:00 | Ivan Penev v Mihnea Petru Zaharia | 6-1,1-6,0-6 |
| 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 |
| 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 |