Stadium: COURT VIKTOR TROICKI Round: 25 Ground: Clay
| UTR Pro Sofia | 2023/09/10 07:00 | Petr Nesterov v Gabriel Donev | 7-6,3-0 |
| UTR Pro Sofia | 2023/09/09 08:52 | Hernando J E Isnardi v Gabriel Donev | 2-6,3-6 |
| UTR Pro Sofia | 2023/09/08 05:00 | Gabriel Donev v Milen Ianakiev | 6-3,5-2 |
| UTR Pro Sofia | 2023/09/07 06:30 | Gabriel Donev v Christos Keisidis | 6-3,6-2 |
| UTR Pro Sofia | 2023/09/06 05:00 | Janos Fekete v Gabriel Donev | 0-6,6-3,3-6 |
| UTR Pro Sofia | 2023/09/05 09:02 | Sergo Sikharulidze v Gabriel Donev | 0-6,3-6 |
| ITF M15 Kursumlijska Banja | 2023/08/30 09:05 | Gabriel Donev v Alessandro Bellifemine | 3-6,6-4,2-6 |
| ITF M15 Targu Jiu | 2023/08/15 13:45 | Lorenzo Joaquin Rodriguez v Gabriel Donev | 6-7,7-6,6-4 |
| ITF M15 Kursumlijska Banja | 2023/09/17 10:30 | Svyatoslav Gulin v Dusan Obradovic | 2-6,3-6 |
| ITF M15 Kursumlijska Banja | 2023/09/16 08:30 | Francesco Ferrari v Dusan Obradovic | 2-6,1-6 |
| ITF M15 Kursumlijska Banja | 2023/09/15 09:00 | Vlad Andrei Dancu v Dusan Obradovic | 6-3,3-6,2-6 |
| ITF M15 Kursumlijska Banja | 2023/09/14 10:20 | Dusan Obradovic v Nicolas Buitrago | 6-2,6-2 |
| ITF M15 Kursumlijska Banja | 2023/09/13 13:20 | Dusan Obradovic v Milan Drinic | 7-5,3-6,6-1 |
| ITF M15 Pirot | 2023/09/09 10:30 | Filip Cristian Jianu v Dusan Obradovic | 6-3,6-1 |
| ITF M15 Pirot | 2023/09/08 09:50 | Antonio Massara v Dusan Obradovic | 2-6,2-6 |
| ITF M15 Pirot | 2023/09/07 07:30 | Francesco Ferrari v Dusan Obradovic | 1-6,2-6 |