Stadium: Court 7 Round: 28 Ground: Clay
| ITF M15 Kursumlijska Banja | 2023/09/22 08:00 | Andrey Chepelev v Luka Pavlovic | 3-6,2-6 |
| ITF M15 Kursumlijska Banja | 2023/09/21 09:50 | Mihai Alexandru Coman v Luka Pavlovic | 4-6,1-6 |
| ITF M15 Kursumlijska Banja | 2023/09/19 10:35 | Vuk Radjenovic v Luka Pavlovic | 3-6,3-6 |
| ITF M15 Kursumlijska Banja | 2023/09/16 08:00 | Luka Pavlovic v Svyatoslav Gulin | 1-6,1-6 |
| ITF M15 Kursumlijska Banja | 2023/09/15 12:55 | Luka Pavlovic v Aldin Setkic | 2-6,6-2,6-3 |
| ITF M15 Kursumlijska Banja | 2023/09/14 11:20 | Andrey Chepelev v Luka Pavlovic | 2-6,1-6 |
| ITF M15 Kursumlijska Banja | 2023/09/12 12:35 | Luka Pavlovic v Mihai Alexandru Coman | 6-1,6-2 |
| ITF M15 Pirot | 2023/09/08 08:00 | Luka Pavlovic v Vlad Andrei Dancu | 6-3,6-7,4-6 |
| ITF M15 Kursumlijska Banja | 2023/09/22 10:00 | Yanaki Milev v Petr Nesterov | 6-2,6-3 |
| ITF M15 Kursumlijska Banja | 2023/09/21 09:30 | Yanaki Milev v Erik Arutiunian | 6-3,6-4 |
| ITF M15 Kursumlijska Banja | 2023/09/20 08:30 | Yanaki Milev v Aleksa Pisaric | 7-6,6-2 |
| Davis Cup | 2023/09/16 12:40 | Yanaki Milev v Alexander Bublik | 4-6,1-6 |
| Challenger Tulln | 2023/09/03 10:25 | Lukas Rosol v Yanaki Milev | 6-4,6-1 |
| Challenger Prague | 2023/08/20 09:25 | Jakub Nicod v Yanaki Milev | 4-6,6-1,6-2 |
| Challenger Banja Luka | 2023/08/07 15:50 | Akira Santillan v Yanaki Milev | 2-6,6-1,6-3 |
| Challenger Banja Luka | 2023/08/07 11:45 | Drazen Petrovic v Yanaki Milev | 3-6,4-6 |