Stadion: Court 22 Round: 25 Ground: Clay
| UTR Pro Tennis Series - Bukarest | 2021/12/04 11:00 | Gabriel Donev v Simon A Ivanov | 6-4,3-6,1-6 |
| ITF - M15 - Antalya | 2023/04/18 07:00 | Gabriel Donev v Maik Steiner | 6-2,4-6,12-10 |
| ITF - M15 - Antalya | 2023/04/17 08:45 | Gabriel Donev v Lucas Obeid | 6-2,6-0 |
| ITF - M15 - Antalya | 2023/04/16 07:00 | Gabriel Donev v Dominique Graf | 6-3,6-0 |
| ITF - M15 - Heraklion | 2023/03/14 07:00 | Niccolo Catini v Gabriel Donev | 6-3,6-3 |
| ITF - M15 - Antalya | 2023/03/08 08:50 | Rrezart Cungu v Gabriel Donev | 6-3,7-5 |
| ITF - M15 - Antalya | 2023/03/07 08:50 | Gabriel Donev v Joao Eduardo Schiessl | 6-4,7-5 |
| ITF - M15 - Antalya | 2023/03/06 12:55 | Gabriel Donev v Aleksandar Mitric | 6-3,6-0 |
| ITF - M15 - Antalya | 2023/03/05 06:30 | Gabriel Donev v Enzo Lima | 6-4,6-1 |
| ITF - M25 - Dubrovnik | 2023/04/07 12:30 | Duje Ajdukovic v Simon A Ivanov | 6-1,6-4 |
| ITF - M25 - Dubrovnik | 2023/04/06 08:00 | Simon A Ivanov v Oleg Prihodko | 6-3,6-4 |
| ITF - M25 - Dubrovnik | 2023/04/05 12:10 | Josip Simundza v Simon A Ivanov | 2-6,4-6 |
| ITF - M15 - Heraklion | 2023/03/21 11:25 | Simon A Ivanov v Yuichiro Inui | 5-7,3-6 |
| ITF - M15 - Heraklion | 2023/03/16 10:45 | Simon A Ivanov v Aleksi Lofman | 3-6,6-1,6-7 |
| ITF - M15 - Heraklion | 2023/03/14 09:55 | Simon A Ivanov v Yuichiro Inui | 6-1,6-4 |
| ITF - M15 - Antalya | 2023/03/08 11:40 | Arthur Reymond v Simon A Ivanov | 6-2,6-4 |
| ITF - M25 - Torelló | 2023/02/28 10:40 | Daniel Merida Aguilar v Simon A Ivanov | 2-6,6-4,6-2 |