Stadium: Court 3 Round: 27 Ground: Clay
| ITF M25 Pazardzhik | 2023/09/28 11:15 | Stefanos Sakellaridis v Nikola Kolyachev | 4-6,4-6 |
| ITF M25 Pazardzhik | 2023/09/27 12:35 | Nikola Kolyachev v Maxwell Benson | 6-4,7-6 |
| ITF M25 Pazardzhik | 2023/09/25 10:00 | Nikola Kolyachev v Martin Dimitrov | 6-4,6-2 |
| ITF M25 Pazardzhik | 2023/09/25 07:00 | Nikola Kolyachev v Vladimir Kravec | 6-0,6-1 |
| ITF M15 Pirot | 2023/09/05 07:25 | Alexander Chepik v Nikola Kolyachev | 6-4,2-6,10-8 |
| ITF M15 Pirot | 2023/09/04 08:30 | Nikola Mitrovic v Nikola Kolyachev | 3-6,0-6 |
| ITF M15 Targu Jiu | 2023/08/15 10:40 | Radovan Michalik v Nikola Kolyachev | 6-2,4-6,11-9 |
| ITF M15 Targu Jiu | 2023/08/13 06:30 | Nikola Kolyachev v Gheorghe Claudiu Schinteie | 6-1,7-6 |
| 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 |
| Challenger Tulln | 2023/09/03 10:25 | Lukas Rosol v Yanaki Milev | 6-4,6-1 |