Stadium: Court 2 Round: 25 Ground: Clay
| ATP Sofia | 2023/11/04 10:05 | Yanaki Milev v Nerman Fatic | 3-6,1-6 |
| ITF M25 Pazardzhik | 2023/10/04 10:25 | Nicholas David Ionel v Yanaki Milev | 6-2,6-3 |
| ITF M25 Pazardzhik | 2023/10/01 07:00 | Yanaki Milev v Clement Tabur | 2-6,6-3,2-6 |
| ITF M25 Pazardzhik | 2023/09/30 09:40 | Andrey Chepelev v Yanaki Milev | 4-6,3-6 |
| ITF M25 Pazardzhik | 2023/09/29 08:40 | Nikola Kolyachev v Yanaki Milev | 0-6,0-6 |
| ITF M25 Pazardzhik | 2023/09/28 08:15 | Yanaki Milev v Eric Vanshelboim | 6-2,7-5 |
| ITF M25 Pazardzhik | 2023/09/27 07:00 | Yanaki Milev v Jasza Szajrych | 7-6,7-5 |
| ITF M15 Kursumlijska Banja | 2023/09/23 08:00 | Luka Pavlovic v Yanaki Milev | 6-3,6-4 |
| ITF M15 Antalya | 2023/11/09 07:00 | Evgeny Tyurnev v Stefan Popovic | 2-6,7-5,6-4 |
| ITF M15 Antalya | 2023/11/08 07:00 | Nicholas David Ionel v Evgeny Tyurnev | 1-6,7-6,3-6 |
| Challenger Istanbul | 2023/09/03 13:15 | Evgeny Tyurnev v Saba Purtseladze | 7-5,1-6,3-6 |
| Challenger Astana | 2023/07/24 09:45 | Mikhail Kukushkin v Evgeny Tyurnev | 6-2,6-0 |
| ITF M25 Kursumlijska Banja | 2023/06/08 10:05 | Lautaro Midon v Evgeny Tyurnev | 2-6,7-5,6-4 |
| ITF M15 Kursumlijska Banja | 2023/05/26 08:00 | Andrea Picchione v Evgeny Tyurnev | 4-6,6-0,6-3 |
| ITF M15 Kursumlijska Banja | 2023/05/25 09:20 | Evgeny Tyurnev v Ignacio Monzon | 7-5,6-0 |
| ITF M15 Kursumlijska Banja | 2023/05/24 08:45 | Aleksa Pisaric v Evgeny Tyurnev | 4-6,5-7 |