Stadium: Court 1 Round: 14 Ground: Clay
| ITF M25 Poprad | 2023/06/22 08:00 | Lukas Palovic v Milos Karol | 2-6,6-3,6-4 |
| ITF M25 Poprad | 2023/06/21 09:55 | Milos Karol v Alibek Kachmazov | 7-5,6-4 |
| Challenger Bratislava | 2023/06/12 15:00 | Vitaliy Sachko v Milos Karol | 6-4,6-1 |
| Challenger Bratislava | 2023/06/12 09:55 | Milos Karol v Ulises Blanch | 4-6,7-6,6-4 |
| Challenger Prostejov | 2023/06/04 09:15 | Milos Karol v Vitaliy Sachko | 3-6,2-6 |
| ITF M25 Jablonec Nad Nisou | 2023/05/28 11:30 | Milos Karol v Thijmen Loof | 5-7,2-6 |
| ITF M25 Most | 2023/05/24 12:45 | Milos Karol v Mika Brunold | 2-6,4-6 |
| ITF M15 Prijedor | 2023/05/17 13:15 | Milos Karol v Ali Habib | 4-6,6-1,3-10 |
| Challenger Karlsruhe | 2023/07/02 13:25 | Tim Handel v Vladyslav Orlov | 6-4,6-4 |
| ITF M25 Arlon | 2023/06/28 09:30 | Vladyslav Orlov v Facundo Juarez | 3-6,2-6 |
| ITF M25 Poprad | 2023/06/24 07:55 | Vladyslav Orlov v Patrik Rikl | 4-6,2-6 |
| ITF M25 Poprad | 2023/06/23 08:00 | Sebastian Sec v Vladyslav Orlov | 2-6,6-7 |
| ITF M25 Poprad | 2023/06/22 08:00 | Roman Postolka v Vladyslav Orlov | 3-6,4-6 |
| ITF M25 Poprad | 2023/06/20 09:40 | Brandon Walkin v Vladyslav Orlov | 3-6,4-6 |
| ATP Stuttgart | 2023/06/10 12:30 | Vladyslav Orlov v Antoine Bellier | 3-6,4-6 |
| Challenger Heilbronn | 2023/06/05 10:30 | Sebastian Fanselow v Vladyslav Orlov | 6-3,3-6,6-3 |