Stadium: Court 3 Round: 26 Ground: Clay
| ITF - M25 Pazardzhik | 2023/10/03 08:10 | Viktor Kirov v Andrey Chepelev | 4-6,2-6 |
| ITF - M25 Pazardzhik | 2023/09/30 09:40 | Andrey Chepelev v Yanaki Milev | 4-6,3-6 |
| ITF - M25 Pazardzhik | 2023/09/29 08:45 | 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 - M25 Pazardzhik | 2023/09/28 07:00 | Nicholas David Ionel v Simon A Ivanov | 6-0,6-1 |
| ITF M15 - Pirot | 2023/09/08 08:00 | Simon A Ivanov v Peter Fajta | 2-6,6-7 |
| ITF M15 - Pirot | 2023/09/07 07:30 | Simon A Ivanov v Erik Arutiunian | 7-6,4-6,6-0 |
| ITF M15 - Pirot | 2023/09/06 07:30 | Simon A Ivanov v Marco Furlanetto | 3-6,7-6,7-5 |
| ITF - M15 Kursumlijska Banja | 2023/08/29 12:20 | Simon A Ivanov v Giannicola Misasi | 6-7,3-6 |
| ITF - M15 Targu Jiu | 2023/08/18 07:00 | Juan Pablo Paz v Simon A Ivanov | 6-3,6-7,6-4 |
| ITF - M15 Targu Jiu | 2023/08/17 07:55 | Calin Manda v Simon A Ivanov | 3-6,6-4,3-6 |
| ITF - M15 Targu Jiu | 2023/08/16 07:00 | Marc Majdandzic v Simon A Ivanov | 1-6,2-6 |