Stadium: Court 1 Round: 26 Ground: Hardcourt outdoor
| ITF M15 Monastir | 2023/08/29 10:35 | Ilia Simakin v Matteo Covato | 6-2,6-3 |
| ITF M15 Monastir | 2023/08/22 11:35 | Luca Fantini v Ilia Simakin | 5-7,6-4,6-2 |
| ITF M25 Astana | 2023/08/03 05:40 | Filip Peliwo v Ilia Simakin | 7-5,6-4 |
| ITF M25 Astana | 2023/08/02 08:30 | Arslanbek Aitkulov v Ilia Simakin | 3-6,4-6 |
| Challenger Astana | 2023/07/24 05:40 | Ilia Simakin v Egor Gerasimov | 6-7,6-4,5-7 |
| Challenger Astana | 2023/07/23 10:15 | Ilia Simakin v Siddhant Banthia | 2-6,6-2,6-3 |
| ITF M15 Antalya | 2023/05/10 10:55 | Max Alcala Gurri v Ilia Simakin | 6-0,6-4 |
| ITF M15 Antalya | 2023/05/09 07:30 | Ilia Simakin v Mert Naci Turker | 2-6,6-4,10-7 |
| ITF M15 Monastir | 2023/08/30 10:10 | Victor Kuznetsov v Leopold Zima | 1-6,1-6 |
| ITF M15 Monastir | 2023/08/22 11:50 | Martin Landaluce v Leopold Zima | 6-7,6-1,6-4 |
| ITF M15 Eupen | 2023/08/09 11:25 | Maik Steiner v Leopold Zima | 6-3,6-3 |
| ITF M15 Metzingen | 2023/07/26 11:00 | Leopold Zima v Yannik Kelm | 5-7,6-2,1-6 |
| ITF M25 Klosters | 2023/07/06 11:45 | Benjamin Lock v Leopold Zima | 6-3,6-7,6-2 |
| ITF M25 Cattolica | 2023/06/21 12:00 | Leopold Zima v Julian Ocleppo | 6-7,0-6 |
| ITF M25 Cattolica | 2023/06/20 13:40 | Leopold Zima v Marco De Rossi | 6-3,4-6,6-2 |
| ITF M25 Cordoba | 2023/06/05 16:00 | Leopold Zima v Sam K Baumgartner | 6-4,6-2 |