Stadium: Court 1 Round: 44 Ground: Clay
| ITF M15 Pirot | 2023/09/04 07:30 | Obrad Markovski v Maxim Krapivin | 1-6,6-4,10-5 |
| 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 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 Pirot | 2023/09/04 07:30 | Ioannis Kountourakis v Lorenzo Vatteroni | 6-2,6-3 |
| ITF M15 Pirot | 2023/09/03 10:00 | Mal Agushi v Ioannis Kountourakis | 5-7,3-6 |
| ITF M15 Kursumlijska Banja | 2023/08/31 11:20 | Ioannis Kountourakis v Dusan Obradovic | 4-6,6-7 |
| ITF M15 Kursumlijska Banja | 2023/08/30 13:45 | Nikola Djosic v Ioannis Kountourakis | 4-6,7-6,1-6 |
| 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 | Lorenzo Vatteroni v Ioannis Kountourakis | 6-0,3-6,9-11 |
| ITF M15 Metzingen | 2023/07/23 07:30 | Ioannis Kountourakis v Stepan Mruzek | 3-6,5-7 |
| ITF M15 Sofia | 2023/07/03 09:30 | Ioannis Kountourakis v Adam Heinonen | 6-7,5-7 |