Stadium: Court 2 Round: 44 Ground: Clay
| ITF - M25 Telavi | 2023/10/16 06:00 | Jasza Szajrych v Arystanbek Kaparov | 6-0,6-1 |
| ITF - M25 Pazardzhik | 2023/10/04 10:15 | Jasza Szajrych v Plamen Milushev | 6-3,6-7,5-7 |
| ITF - M25 Pazardzhik | 2023/09/27 07:00 | Yanaki Milev v Jasza Szajrych | 7-6,7-5 |
| 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 - M25 Telavi | 2023/10/16 06:00 | Dennis Dragomirov v Gheorghe Claudiu Schinteie | 4-6,7-6,10-6 |
| ITF - M25 Telavi | 2023/10/15 06:00 | Dennis Dragomirov v Victor Kuznetsov | 6-2,7-6 |
| ITF - M25 Telavi | 2023/10/10 06:00 | Jeremy Gschwendtner v Dennis Dragomirov | 6-2,6-4 |
| ITF - M15 Bad Waltersdorf | 2023/10/01 07:00 | Tomas Lanik v Dennis Dragomirov | 6-4,6-2 |
| ITF - M15 Buschhausen | 2023/09/11 12:30 | Dennis Dragomirov v Noel Larwig | 3-6,2-6 |
| ITF - M15 Buschhausen | 2023/09/11 08:00 | Taym Alazmeh v Dennis Dragomirov | 6-2,4-6,7-10 |
| ITF - M25 Maribor | 2023/09/04 11:10 | Nikola Puntaric v Dennis Dragomirov | 7-5,6-4 |
| ITF - M15 Vienna | 2023/08/28 08:00 | Janos Fekete v Dennis Dragomirov | 6-2,6-3 |