Stadion: Court 4 Round: 25 Ground: Clay
| ITF - M25 - Pazardzhik | 2023/09/27 07:00 | Yanaki Milev v Jasza Szajrych | 7-6,7-5 |
| Challenger - Stettin | 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 - Pazardzhik | 2023/10/02 13:15 | Plamen Milushev v Maxwell Benson | 6-4,7-5 |
| ITF - M25 - Pazardzhik | 2023/10/02 07:30 | Razvan Baiant v Plamen Milushev | 4-6,6-4,5-10 |
| ITF - M25 - Pazardzhik | 2023/09/27 10:55 | Hynek Barton v Plamen Milushev | 6-3,6-3 |
| ITF - M25 - Pazardzhik | 2023/09/25 12:00 | Plamen Milushev v Andrea Meduri | 1-6,7-6,10-7 |
| ITF - M25 - Pazardzhik | 2023/09/24 07:00 | Razvan Baiant v Plamen Milushev | 6-4,1-6,3-10 |
| ITF - M15 - Sofia | 2023/07/02 06:30 | Plamen Milushev v Pierre Yves Bailly | 6-7,2-6 |
| ITF - M15 - Sofia | 2022/07/03 09:00 | Martin Dimitrov v Plamen Milushev | 7-6,6-3 |
| UTR Pro Tennis Series - Kopenhagen | 2022/04/30 10:30 | Martin Dimitrov v Plamen Milushev | 4-6,7-5,5-2 |