Stadium: Court 3 Round: 28 Ground: Clay
| ITF M25 Pazardzhik | 2023/09/29 08:45 | Nicholas David Ionel v Andrey Chepelev | 4-6,6-4,5-7 |
| ITF M25 Pazardzhik | 2023/09/28 09:40 | Roman Postolka v Andrey Chepelev | 5-7,6-7 |
| ITF M25 Pazardzhik | 2023/09/26 08:30 | Aleksander Chayka v Andrey Chepelev | 3-6,0-6 |
| ITF M15 Kursumlijska Banja | 2023/09/22 08:00 | Andrey Chepelev v Luka Pavlovic | 3-6,2-6 |
| ITF M15 Kursumlijska Banja | 2023/09/21 09:25 | Andrey Chepelev v Gabriel Donev | 6-4,7-6 |
| ITF M15 Kursumlijska Banja | 2023/09/20 09:10 | Andrey Chepelev v Zoran Ludoski | 3-6,6-1,6-1 |
| ITF M15 Kursumlijska Banja | 2023/09/14 11:20 | Andrey Chepelev v Luka Pavlovic | 2-6,1-6 |
| ITF M15 Kursumlijska Banja | 2023/09/13 09:50 | Andrey Chepelev v Viktor Jovic | 3-6,7-5,7-6 |
| 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 M15 Kursumlijska Banja | 2023/09/21 09:30 | Yanaki Milev v Erik Arutiunian | 6-3,6-4 |
| ITF M15 Kursumlijska Banja | 2023/09/20 08:30 | Yanaki Milev v Aleksa Pisaric | 7-6,6-2 |
| Davis Cup | 2023/09/16 12:40 | Yanaki Milev v Alexander Bublik | 4-6,1-6 |