| UTR Pro Tennis Series Zadar | 2021/11/15 13:30 | Ivan Penev v Vladan Tadic | 4-6,6-4,0-6 |
| UTR Pro Tennis Series Zadar | 2021/11/14 12:00 | Alen Rogic-Hadzalic v Ivan Penev | 6-3,4-6,6-2 |
| ITF M15 Sozopol | 2021/10/11 09:00 | Ivan Penev v Berk Ilkel | 6-7,6-1,8-10 |
| ITF M15 Sozopol | 2021/10/10 09:00 | Ivan Penev v Gianluca Coloma-Heck | 6-1,6-3 |
| ITF M15 Sozopol | 2021/10/04 07:00 | Yann Wojcik v Ivan Penev | 3-6,7-5,10-2 |
| ITF M15 Sozopol | 2021/09/13 10:30 | Tommaso Compagnucci v Ivan Penev | 6-2,6-3 |
| ITF M15 Sozopol | 2021/09/12 10:00 | Radu F Macovei v Ivan Penev | 4-6,3-6 |
| UTR Pro Tennis Series Sofia | 2021/09/01 11:00 | Samuil Konov v Ivan Penev | 4-6,6-1,6-0 |
| UTR Pro Tennis Series Zadar | 2021/11/15 15:00 | Alen Rogic-Hadzalic v Oleksii Osadchyi | 6-0,5-1 |
| UTR Pro Tennis Series Zadar | 2021/11/14 13:00 | Vladan Tadic v Oleksii Osadchyi | 6-0,6-1 |