Round: 62 Ground: Clay
| UTR Pro Tennis Series Blaricum | 2022/04/08 12:30 | Ivan Penev v Ivan Denisov | 2-5 |
| UTR Pro Tennis Series Blaricum | 2022/04/07 12:30 | Ivan Penev v Roland Stuurman | 6-3,3-6,6-6 |
| UTR Pro Tennis Series Blaricum | 2022/04/06 08:00 | Ivan Penev v Vladimir Popov | 6-3,6-7,6-7 |
| UTR Pro Tennis Series Blaricum | 2022/04/05 11:00 | Miko Wassermann v Ivan Penev | 6-3,4-6,6-3 |
| UTR Pro Tennis Series Blaricum | 2022/04/04 13:30 | Marcel Zielinski v Ivan Penev | 6-0,6-4 |
| UTR Pro Tennis Series Barcelona | 2022/04/02 07:30 | Ivan Penev v David Jorda Sanchis | 1-6,3-5 |
| UTR Pro Tennis Series Barcelona | 2022/03/31 14:08 | Ivan Penev v Plamen Milushev | 6-2,1-0 |
| UTR Pro Tennis Series Barcelona | 2022/03/31 09:30 | Ivan Penev v Jordi Mas De Ugarte | 3-6,4-5 |
| ITF M15 Antalya | 2023/05/14 12:00 | Ruben Gospodjinacki v Aleksander Chayka | 2-6,4-6 |
| ITF M15 Antalya | 2023/05/08 09:15 | Alexandr Binda v Ruben Gospodjinacki | 6-4,6-3 |
| ITF M15 Antalya | 2023/05/07 07:00 | Ivan Zaytsev v Ruben Gospodjinacki | 6-1,6-3 |
| ITF M15 Antalya | 2023/04/24 13:15 | Daniel Ibragimov v Ruben Gospodjinacki | 6-3,6-2 |
| ITF M15 Antalya | 2023/04/23 07:00 | Ruben Gospodjinacki v Imran Sibille | 7-6,6-3 |
| ITF M15 Antalya | 2023/03/26 08:00 | Vasile Antonescu v Ruben Gospodjinacki | 6-3,6-1 |
| ITF M15 Antalya | 2023/03/19 07:00 | Valentin Vanta v Ruben Gospodjinacki | 6-0,6-2 |
| ITF M25 Antalya | 2023/01/30 11:10 | Yamato Sueoka v Ruben Gospodjinacki | 6-3,6-3 |