Stadium: Serena Maniva Centre Round: 25 Ground: Clay
| Challenger - Lüdenscheid | 2023/08/01 08:00 | Vladyslav Orlov v Tommaso Compagnucci | 5-7,7-6,4-6 |
| Challenger - Lüdenscheid | 2023/07/30 13:10 | Vladyslav Orlov v Moritz Pieper | 6-4,6-2 |
| Challenger Zug | 2023/07/24 12:10 | Gianmarco Ferrari v Vladyslav Orlov | 6-3,6-4 |
| Challenger Zug | 2023/07/23 15:25 | Vladyslav Orlov v Ugo Blanchet | 4-6,6-4,7-6 |
| Challenger - Tampere | 2023/07/17 11:05 | Vladyslav Orlov v Ergi Kirkin | 6-7,3-6 |
| Challenger - Tampere | 2023/07/16 10:30 | Vladyslav Orlov v Vesa Ahti | 6-4,6-4 |
| Challenger - Salzburg | 2023/07/10 09:00 | Akira Santillan v Vladyslav Orlov | 6-3,6-1 |
| Challenger - Salzburg | 2023/07/09 10:10 | Milos Karol v Vladyslav Orlov | 7-5,3-6,1-6 |
| Challenger Zug | 2023/07/28 13:00 | Matteo Gigante v Joris De Loore | 6-3,6-7,4-6 |
| Challenger Zug | 2023/07/27 08:30 | Dimitar Kuzmanov v Matteo Gigante | 4-6,6-7 |
| Challenger Zug | 2023/07/26 13:45 | Dalibor Svrcina v Matteo Gigante | 1-6,7-6,3-6 |
| Challenger - Triëst | 2023/07/19 14:45 | Fabian Marozsan v Matteo Gigante | 7-6,3-6,7-5 |
| Challenger - Triëst | 2023/07/18 08:00 | Clement Tabur v Matteo Gigante | 4-6,7-6,3-6 |
| Challenger - San Benedetto | 2023/07/11 13:50 | Michael Geerts v Matteo Gigante | 4-6,6-4,6-4 |
| Challenger - Milaan | 2023/07/09 14:30 | Facundo Diaz Acosta v Matteo Gigante | 6-3,6-3 |
| Challenger - Milaan | 2023/07/08 15:45 | Matteo Gigante v Luciano Darderi | 6-4,3-6,7-5 |