| UTR Pro Thessaloniki | 2023/04/24 05:00 | Mihai Razvan Marinescu v Jakub Ostajewski | 6-3,5-0 |
| UTR Pro Florida | 2023/04/02 13:00 | Azariah Rusher v Jakub Ostajewski | 3-6,6-7 |
| UTR Pro Copenhagen | 2023/02/18 07:00 | Jakub Ostajewski v Cornelius Alexander Shalmi | 2-6,4-6 |
| UTR Pro Copenhagen | 2023/02/17 08:30 | Hugo Pierre v Jakub Ostajewski | 6-0,6-0 |
| UTR Pro Copenhagen | 2023/02/16 12:00 | Igor Skoric v Jakub Ostajewski | 1-6,1-6 |
| UTR Pro Copenhagen | 2023/02/15 07:00 | Wadym Konowczuk v Jakub Ostajewski | 4-6,1-6 |
| UTR Pro Copenhagen | 2023/02/13 12:45 | Ivan Sodan v Jakub Ostajewski | 6-3,7-6 |
| ITF M15 Palm Coast | 2023/02/06 16:30 | Jakub Ostajewski v Benjamin Denis Alarcon | 4-6,3-6 |
| UTR Pro Beograd | 2023/04/23 06:00 | Vladimir Filip v Matija Samardzic | 3-6,2-6 |
| UTR Pro Beograd | 2023/04/22 07:30 | Hugo Pierre v Vladimir Filip | 3-6,5-6 |
| UTR Pro Beograd | 2023/04/21 07:30 | Vladimir Filip v Dusan Obradovic | 2-6,2-6 |
| UTR Pro Beograd | 2023/04/20 07:30 | Vladimir Filip v Obrad Markovski | 5-7,3-6 |
| UTR Pro Beograd | 2023/04/19 06:00 | Tadija Radovanovic v Vladimir Filip | 4-6,3-6 |
| UTR Pro Beograd | 2023/04/18 09:53 | Aleksei Khomich v Vladimir Filip | 7-5,5-7,2-6 |
| UTR Pro Tennis Series Montrouge | 2022/11/13 08:00 | Rayane Roumane v Vladimir Filip | 0-6,2-5 |
| UTR Pro Tennis Series Montrouge | 2022/11/12 07:00 | Nathan Guiovanna v Vladimir Filip | 2-6,4-6 |