Stadium: COURT VIKTOR TROICKI Round: 25 Ground: Clay
| ITF M15 Kursumlijska Banja | 2023/05/26 08:00 | Samuel Vincent Ruggeri v Martyn Pawelski | 6-7,6-7 |
| ITF M15 Kursumlijska Banja | 2023/05/25 11:05 | Samuel Vincent Ruggeri v Lorenzo Carboni | 6-3,6-4 |
| ITF M15 Kursumlijska Banja | 2023/05/23 13:00 | Samuel Vincent Ruggeri v Zoran Ludoski | 4-6,6-1,7-5 |
| ITF M25 Kursumlijska Banja | 2023/05/17 09:55 | Samuel Vincent Ruggeri v Marko Topo | 6-3,3-6,1-6 |
| ITF M25 Kursumlijska Banja | 2023/05/13 10:05 | Clement Tabur v Samuel Vincent Ruggeri | 7-6,6-4 |
| ITF M25 Kursumlijska Banja | 2023/05/12 08:00 | Samuel Vincent Ruggeri v Andrey Chepelev | 6-1,6-4 |
| ITF M25 Kursumlijska Banja | 2023/05/11 08:30 | Benjamin Lock v Samuel Vincent Ruggeri | 2-6,6-4,0-6 |
| ITF M25 Kursumlijska Banja | 2023/05/10 07:00 | Samuel Vincent Ruggeri v Simone Agostini | 7-5,6-2 |
| ITF M15 Kursumlijska Banja | 2023/05/30 09:05 | Geni Inoue v Obrad Markovski | 4-6,2-6 |
| ITF M15 Kursumlijska Banja | 2023/05/29 11:30 | Federico Hernan Giovanniello v Obrad Markovski | 4-6,2-6 |
| Challenger Skopje | 2023/05/22 09:00 | Karol Drzewiecki v Obrad Markovski | 6-2,7-5 |
| 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 |