Stadium: Centre Court Round: 19 Ground: Clay
| Challenger Skopje | 2023/05/21 09:00 | Karol Drzewiecki v Besir Durguti | 6-2,6-1 |
| Challenger Ostrava | 2023/04/23 14:35 | Karol Drzewiecki v Filip Peliwo | 1-6,6-3,6-7 |
| Challenger Biel | 2023/03/20 13:45 | Karol Drzewiecki v Kirill Kivattsev | 4-6,3-6 |
| Challenger Biel | 2023/03/19 17:30 | Ramkumar Ramanathan v Karol Drzewiecki | 4-6,7-5,2-6 |
| Challenger Concepcion | 2023/01/23 14:00 | Juan Bautista Torres v Karol Drzewiecki | 6-1,2-6,6-2 |
| Challenger Concepcion | 2023/01/22 15:30 | Karol Drzewiecki v Yunseong Chung | 6-3,6-2 |
| Challenger Guayaquil | 2022/10/31 16:25 | Karol Drzewiecki v Colin Markes | 4-6,6-4,6-7 |
| Challenger Coquimbo | 2022/10/16 18:00 | Karol Drzewiecki v Sumit Nagal | 3-6,2-6 |
| Challenger Skopje | 2023/05/21 10:15 | Obrad Markovski v Evgeny Karlovskiy | 6-2,6-1 |
| ITF M15 Osijek | 2023/05/02 09:45 | Obrad Markovski v Michael Gloeckler | 5-7,2-6 |
| ITF M15 Osijek | 2023/05/01 13:00 | Obrad Markovski v Jiri Krouzek | 7-5,6-4 |
| UTR Pro Beograd | 2023/04/22 09:51 | Maxime Hamou v Obrad Markovski | 3-6,7-5,6-3 |
| UTR Pro Beograd | 2023/04/21 06:00 | Aleksei Khomich v Obrad Markovski | 3-6,0-0 |
| UTR Pro Beograd | 2023/04/20 07:30 | Vladimir Filip v Obrad Markovski | 5-7,3-6 |
| UTR Pro Beograd | 2023/04/18 08:05 | Tadija Radovanovic v Obrad Markovski | 3-6,6-7 |
| UTR Pro Beograd | 2023/04/17 06:00 | Obrad Markovski v Dusan Obradovic | 1-6,7-5,4-6 |