Stadium: Court 21 Round: 25 Ground: Clay
| 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 Kursumlijska Banja | 2023/09/22 10:00 | Yanaki Milev v Petr Nesterov | 6-2,6-3 |
| ITF M25 Santa Margherita | 2023/10/11 09:20 | Niccolo Catini v Giovanni Fonio | 2-6,3-6 |
| ITF M25 Santa Margherita | 2023/10/10 09:55 | Niccolo Catini v Giammarco Gandolfi | 7-5,6-4 |
| ITF M25 Santa Margherita | 2023/10/09 07:55 | Niccolo Catini v Mats Hermans | 6-2,6-3 |
| ITF M25 Santa Margherita | 2023/09/24 08:00 | Francesco Liucci v Niccolo Catini | 1-6,3-6 |
| ITF M25 Santa Margherita | 2023/09/21 08:30 | Niccolo Catini v Giovanni Oradini | 5-7,2-6 |
| ITF M25 Santa Margherita | 2023/09/20 08:30 | Niccolo Catini v Niccolo Baroni | 6-2,6-4 |
| ITF M25 Santa Margherita | 2023/09/19 10:20 | Lorenzo Rottoli v Niccolo Catini | 6-7,4-6 |
| ITF M25 Santa Margherita | 2023/09/18 08:30 | Niccolo Catini v Marco Dessi | 6-3,6-3 |