Stadium: Svijany Court Round: 19 Ground: Clay
| Challenger Liberec | 2023/07/30 14:40 | Michael Vrbensky v Dominik Kellovsky | 6-1,6-2 |
| Challenger Zug | 2023/07/24 11:40 | Manuel Guinard v Michael Vrbensky | 6-0,7-6 |
| Challenger Zug | 2023/07/23 11:50 | Kirill Kivattsev v Michael Vrbensky | 2-6,2-6 |
| Challenger Amersfoort | 2023/07/18 15:25 | Michael Vrbensky v Titouan Droguet | 1-6,4-6 |
| Challenger Amersfoort | 2023/07/17 10:15 | Michael Vrbensky v Simon Beaupain | 6-4,2-6,7-6 |
| Challenger Amersfoort | 2023/07/16 15:05 | Michael Vrbensky v Maxime Mora | 6-3,6-4 |
| Challenger Iasi | 2023/07/13 12:00 | Michael Vrbensky v Vitaliy Sachko | 1-6,2-6 |
| Challenger Iasi | 2023/07/11 12:10 | Michael Vrbensky v Juan Bautista Otegui | 6-2,6-3 |
| Challenger Liberec | 2023/07/30 13:00 | Jonas Forejtek v Yanaki Milev | 3-6,4-6 |
| Challenger Amersfoort | 2023/07/16 14:55 | Ryan Nijboer v Yanaki Milev | 6-0,6-3 |
| Challenger Braunschweig | 2023/07/10 11:50 | Yanaki Milev v Denis Yevseyev | 6-7,6-3,3-6 |
| Challenger Braunschweig | 2023/07/09 14:30 | Alvaro Lopez San Martin v Yanaki Milev | 6-3,6-7,4-6 |
| ITF M25 Marburg | 2023/07/05 14:40 | Michael Agwi v Yanaki Milev | 7-5,6-3 |
| Challenger Parma | 2023/06/18 08:00 | Yanaki Milev v Akira Santillan | 1-6,6-4,6-7 |
| ITF M25 Skopje | 2023/06/06 11:05 | Yanaki Milev v Neil Oberleitner | 4-6,4-6 |
| Challenger Skopje | 2023/05/21 09:50 | Yanaki Milev v Pedro Boscardin Dias | 2-6,6-7 |