Ground: Hardcourt outdoor
| ITF M15 Kursumlijska Banja | 2023/08/30 13:35 | Obrad Markovski v Aleksa Pisaric | 4-6,5-7 |
| Davis Cup | 2023/06/17 09:00 | Marco De Rossi v Obrad Markovski | 6-0,6-1 |
| Davis Cup | 2023/06/16 08:50 | Menelaos Efstathiou v Obrad Markovski | 6-1,6-2 |
| Davis Cup | 2023/06/14 07:25 | Obrad Markovski v Alex De Gabriele | 6-4,2-6,6-7 |
| ITF M25 Skopje | 2023/06/07 09:00 | Lazar Vojinovic v Obrad Markovski | 6-3,6-4 |
| ITF M15 Kursumlijska Banja | 2023/05/31 13:50 | Samuel Vincent Ruggeri v Obrad Markovski | 6-4,6-1 |
| 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 |