Stadium: Court 5 Round: 19 Ground: Clay
| Challenger Braunschweig | 2023/07/09 14:30 | Alvaro Lopez San Martin v Yanaki Milev | 6-3,6-7,4-6 |
| ITF M25 Marburg | 2023/07/05 14:40 | Michael Agwi v Yanaki Milev | 7-5,6-3 |
| Challenger Parma | 2023/06/18 08:00 | Yanaki Milev v Akira Santillan | 1-6,6-4,6-7 |
| ITF M25 Skopje | 2023/06/06 11:05 | Yanaki Milev v Neil Oberleitner | 4-6,4-6 |
| Challenger Skopje | 2023/05/21 09:50 | Yanaki Milev v Pedro Boscardin Dias | 2-6,6-7 |
| ITF M15 Antalya | 2023/05/11 07:30 | Deney Wassermann v Yanaki Milev | 6-3,2-6,6-2 |
| ITF M15 Antalya | 2023/05/10 12:20 | Lorenzo Joaquin Rodriguez v Yanaki Milev | 4-6,3-6 |
| ITF M15 Antalya | 2023/05/03 12:15 | Yanaki Milev v Cengiz Aksu | 6-7,3-6 |
| Challenger Braunschweig | 2023/07/09 14:15 | Marc Majdandzic v Denis Yevseyev | 3-6,4-6 |
| Challenger Karlsruhe | 2023/07/04 15:30 | Denis Yevseyev v Thiago Seyboth Wild | 6-4,3-6,3-6 |
| Challenger Karlsruhe | 2023/07/03 10:35 | Denis Yevseyev v Sebastian Fanselow | 7-5,7-6 |
| Challenger Karlsruhe | 2023/07/02 13:50 | Denis Yevseyev v David Fix | 6-3,6-3 |
| Challenger Palmas del Mar | 2023/06/12 20:35 | Denis Yevseyev v Joao Lucas Reis da Silva | 7-5,4-6,5-7 |
| Challenger Tyler | 2023/06/05 23:05 | Denis Yevseyev v Mikhail Kukushkin | 6-7,2-6 |
| Challenger Little Rock | 2023/05/30 20:25 | Alex Michelsen v Denis Yevseyev | 4-6,6-3,7-5 |
| ATP Geneva | 2023/05/20 11:30 | Alessandro Giannessi v Denis Yevseyev | 3-6,6-4,6-2 |