Stadium: Court 3 Round: 26 Ground: Clay
| 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 |
| Challenger Prague | 2023/08/20 09:25 | Jakub Nicod v Yanaki Milev | 4-6,6-1,6-2 |
| ITF M25 Pazardzhik | 2023/09/27 12:20 | George Lazarov v Eric Vanshelboim | 2-6,2-6 |
| ITF M25 Pardubice | 2023/09/23 09:50 | Jonas Forejtek v Eric Vanshelboim | 6-4,6-4 |
| ITF M25 Pardubice | 2023/09/22 08:55 | Eric Vanshelboim v Jiri Barnat | 7-6,3-6,6-4 |
| ITF M25 Pardubice | 2023/09/21 09:25 | Eric Vanshelboim v Daniel Paty | 6-4,7-5 |
| ITF M25 Pardubice | 2023/09/20 09:20 | Eric Vanshelboim v Noel Larwig | 6-2,6-3 |
| ITF M25 Kigali | 2023/09/15 08:00 | Eric Vanshelboim v Guy Orly Iradukunda | 1-6,6-1,3-6 |
| ITF M25 Kigali | 2023/09/14 07:30 | Eric Vanshelboim v Siddhant Banthia | 7-6,7-5 |
| Challenger Banja Luka | 2023/08/09 12:30 | Eric Vanshelboim v Toby Alex Kodat | 5-7,1-6 |