Stadium: Court 3 Round: 44 Ground: Clay
| ITF - M15 Kursumlijska Banja | 2023/08/30 13:35 | Obrad Markovski v Aleksa Pisaric | 4-6,5-7 |
| Cupa Davis | 2023/06/17 09:00 | Marco De Rossi v Obrad Markovski | 6-0,6-1 |
| Cupa Davis | 2023/06/16 08:50 | Menelaos Efstathiou v Obrad Markovski | 6-1,6-2 |
| Cupa Davis | 2023/06/14 07:25 | Obrad Markovski v Alex Degabriele | 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 |
| ITF - M15 Pirot | 2023/09/03 07:30 | Maxim Krapivin v Bogdan Seleznev | 6-2,6-0 |
| ITF - M15 Kursumlijska Banja | 2023/08/29 09:45 | Ioannis Kountourakis v Maxim Krapivin | 6-2,6-4 |
| ITF - M15 Kursumlijska Banja | 2023/08/28 12:00 | Shendrit Deari v Maxim Krapivin | 6-1,4-6,5-10 |
| ITF - M15 Novi Sad | 2023/08/01 07:30 | Maxim Krapivin v Aleksa Mardjonovic | 0-6,5-7 |
| ITF - M15 Novi Sad | 2023/07/30 08:30 | Andrej Radojicic v Maxim Krapivin | 2-6,3-6 |
| ITF - M15 Novi Sad | 2023/07/23 13:00 | Maxim Krapivin v Aljaz Jeran | 2-6,2-6 |
| ITF - M15 Belgrade | 2023/06/26 08:45 | Bogdan Pavel v Maxim Krapivin | 7-6,5-7,10-5 |
| ITF - M15 Belgrade | 2023/06/25 07:00 | Maxim Krapivin v Lazar Vojinovic | 6-4,3-6,10-8 |