Stadium: Court 3 Round: 26 Ground: Clay
| ITF M25 Antalya | 2023/11/15 06:30 | Yanaki Milev v Evgeny Tyurnev | 6-4,7-6 |
| 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 M25 Antalya | 2023/11/15 09:55 | Illya Beloborodko v Alexander Weis | 4-6,4-6 |
| ITF M25 Santa Margherita | 2023/10/28 13:00 | Oriol Roca Batalla v Alexander Weis | 6-2,6-3 |
| ITF M25 Santa Margherita | 2023/10/28 08:30 | Alexander Weis v Carlos Sanchez Jover | 7-6,6-3 |
| ITF M25 Santa Margherita | 2023/10/25 08:00 | Alexander Weis v Gian M Di Natale | 6-0,6-4 |
| ITF M25 Santa Margherita | 2023/10/23 12:00 | Alexander Weis v Alex M Pujolras | 6-2,6-3 |
| ITF M25 Santa Margherita | 2023/10/09 14:30 | Gabriele Pennaforti v Alexander Weis | 5-7,7-5,6-4 |
| Challenger Lisbon | 2023/10/03 15:20 | Alexander Weis v Calvin Hemery | 1-6,3-6 |
| Challenger Lisbon | 2023/10/02 11:45 | Alexander Weis v Henrique Rocha | 3-6,7-6,6-1 |