Stadium: Court 3 Round: 25 Ground: Clay
| ITF M15 Kursumlijska Banja | 2023/09/23 08:00 | Luka Pavlovic v Yanaki Milev | 6-3,6-4 |
| 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 Kupa | 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 Szczecin | 2023/09/10 12:20 | Jasza Szajrych v Henri Squire | 3-6,4-6 |
| ITF M15 Koszalin | 2023/09/07 11:05 | Jasza Szajrych v Petr Brunclik | 4-6,3-6 |
| ITF M15 Koszalin | 2023/09/06 07:30 | Alec Beckley v Jasza Szajrych | 4-6,0-6 |
| ITF M15 Szczawno | 2023/09/03 09:30 | Olaf Pieczkowski v Jasza Szajrych | 6-1,6-2 |
| ITF M15 Szczawno | 2023/09/01 10:35 | Jasza Szajrych v Pawel Juszczak | 6-4,6-0 |
| ITF M15 Szczawno | 2023/08/31 13:30 | Lorenzo Joaquin Rodriguez v Jasza Szajrych | 3-6,6-1,1-6 |
| ITF M15 Szczawno | 2023/08/30 15:30 | Gabriel Matuszewski v Jasza Szajrych | 0-6,2-6 |
| ITF M25 Poznan | 2023/08/24 11:05 | Jeremy Jahn v Jasza Szajrych | 6-2,7-6 |