Estadio: Centre Court Round: 25 Ground: Clay
| Challenger San Benedetto | 2023/07/14 18:00 | Daniel Rincon v Dimitar Kuzmanov | 6-7,6-1,6-4 |
| Challenger San Benedetto | 2023/07/12 15:00 | Michael Geerts v Dimitar Kuzmanov | 3-6,6-1,3-6 |
| Challenger San Benedetto | 2023/07/11 10:00 | Dimitar Kuzmanov v Dmitry Popko | 6-2,6-3 |
| Wimbledon | 2023/06/26 14:00 | Dimitar Kuzmanov v Hyeon Chung | 2-6,6-3,3-6 |
| Challenger de Bratislava | 2023/06/18 11:30 | Dimitar Kuzmanov v Vitaliy Sachko | 6-2,2-6,6-7 |
| Challenger de Bratislava | 2023/06/17 13:25 | Alex Molcan v Dimitar Kuzmanov | 0-6,1-6 |
| Challenger de Bratislava | 2023/06/16 13:40 | Dimitar Kuzmanov v Jerome Kym | 7-5,6-4 |
| Challenger de Bratislava | 2023/06/14 09:00 | Zsombor Piros v Dimitar Kuzmanov | 3-6,6-2,4-6 |
| Challenger de Zug | 2023/07/24 09:00 | Dylan Dietrich v Kyrian Jacquet | 6-2,5-7,6-4 |
| Challenger de Zug | 2023/07/23 09:00 | Giovanni Fonio v Dylan Dietrich | 3-6,3-6 |
| ITF M25 Klosters | 2023/07/06 08:00 | Dylan Dietrich v Jerome Kym | 1-6,6-3,0-6 |
| ITF M25 Klosters | 2023/07/04 07:00 | Jan Sebesta v Dylan Dietrich | 4-6,6-7 |
| ITF M15 Saarlouis | 2023/06/22 09:00 | Hazem Naw v Dylan Dietrich | 6-2,6-0 |
| ITF M15 Saarlouis | 2023/06/20 10:00 | Tadeas Paroulek v Dylan Dietrich | 6-2,5-7,3-6 |
| ITF M15 Duffel | 2023/06/14 08:00 | Dylan Dietrich v Joao Fonseca | 3-6,3-6 |
| ITF M25 Most | 2023/05/25 08:00 | Timo Stodder v Dylan Dietrich | 3-6,6-2,7-5 |