Stadium: Court 8 Round: 27 Ground: Hardcourt indoor
| Challenger Bratislava | 2023/06/14 09:00 | Zsombor Piros v Dimitar Kuzmanov | 3-6,6-2,4-6 |
| Challenger Bratislava | 2023/06/13 10:25 | Gerald Melzer v Dimitar Kuzmanov | 2-6,3-6 |
| Challenger Prostejov | 2023/06/08 12:25 | Dimitar Kuzmanov v Francisco Comesana | 4-6,4-6 |
| Challenger Prostejov | 2023/06/07 13:35 | Hynek Barton v Dimitar Kuzmanov | 6-2,3-6,1-6 |
| Challenger Prostejov | 2023/06/05 16:35 | Lukas Pokorny v Dimitar Kuzmanov | 1-6,0-6 |
| Challenger Troisdorf | 2023/05/30 12:45 | Dimitar Kuzmanov v Sumit Nagal | 3-6,6-1,5-7 |
| French Open | 2023/05/23 11:30 | Emilio Nava v Dimitar Kuzmanov | 6-3,7-6 |
| Challenger Francavilla | 2023/05/10 09:30 | Lorenzo Giustino v Dimitar Kuzmanov | 1-6,7-6,6-2 |
| Challenger Bratislava | 2023/06/14 13:00 | Jerome Kym v Norbert Gombos | 6-3,6-7,7-6 |
| Challenger Bratislava | 2023/06/13 08:30 | Jerome Kym v Henri Laaksonen | 6-2,7-6 |
| Challenger Bratislava | 2023/06/12 11:35 | Jerome Kym v Michael Vrbensky | 6-4,6-2 |
| Challenger Bratislava | 2023/06/11 10:00 | Mate Valkusz v Jerome Kym | 4-6,4-6 |
| Challenger Heilbronn | 2023/06/06 11:45 | Jerome Kym v Felipe Meligeni Rodrigues Alves | 6-7,3-6 |
| Challenger Heilbronn | 2023/06/05 11:00 | Andrea Arnaboldi v Jerome Kym | 6-7,5-7 |
| Challenger Heilbronn | 2023/06/04 14:25 | Sandro Kopp v Jerome Kym | 6-7,6-7 |
| ITF M25 Kiseljak | 2023/06/03 07:55 | Jerome Kym v Duje Ajdukovic | 7-6,1-6,4-6 |