| UTR Pro Tennis Series Sofia | 2021/08/31 06:30 | Martin Dimitrov v Ivan Penev | 1-6,6-3,6-3 |
| UTR Pro Tennis Series Zadar | 2021/11/19 13:50 | Ivan Penev v Alexander Lazov | 6-3,3-6,3-6 |
| UTR Pro Tennis Series Zadar | 2021/11/16 10:30 | Ivan Penev v Oleksii Osadchyi | 6-1,6-1 |
| 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 |
| UTR Pro Tennis Series Barcelona | 2021/12/16 09:00 | Sergio Redondo v Martin Dimitrov | 6-3,6-3 |
| UTR Pro Tennis Series Barcelona | 2021/12/15 13:00 | Pol Del Castillo v Martin Dimitrov | 3-6,6-2,5-4 |
| UTR Pro Tennis Series Barcelona | 2021/12/14 15:26 | Nicolas H Cuesta v Martin Dimitrov | 6-2,5-4 |
| UTR Pro Tennis Series Barcelona | 2021/12/12 11:30 | Vladimir Popov v Martin Dimitrov | 4-6,4-6 |
| UTR Pro Tennis Series Zadar | 2021/11/20 09:00 | Martin Dimitrov v Robert Rumler | 2-6,4-4 |
| UTR Pro Tennis Series Zadar | 2021/11/19 12:00 | Alen Bill v Martin Dimitrov | 7-5,3-6,5-6 |
| UTR Pro Tennis Series Zadar | 2021/11/18 14:30 | Drazen Petrovic v Martin Dimitrov | 6-4,6-4 |
| UTR Pro Tennis Series Zadar | 2021/11/16 09:00 | Myroslav Bondar v Martin Dimitrov | 1-6,4-6 |