Stadium: Court 1 Round: 19 Ground: Clay
| Challenger Zug | 2023/07/23 13:20 | Joao Lucas Reis da Silva v Gianmarco Ferrari | 3-6,6-7 |
| Challenger San Benedetto | 2023/07/11 12:55 | Gianmarco Ferrari v Flavio Cobolli | 3-6,1-6 |
| Challenger Milán | 2023/07/03 15:00 | Facundo Diaz Acosta v Gianmarco Ferrari | 6-0,6-2 |
| Challenger Modena | 2023/06/29 18:00 | Gianmarco Ferrari v Emilio Nava | 1-6,7-6,2-6 |
| Challenger Modena | 2023/06/28 08:30 | Renzo Olivo v Gianmarco Ferrari | 3-6,4-6 |
| Challenger Modena | 2023/06/26 14:30 | Filip Cristian Jianu v Gianmarco Ferrari | 7-6,4-6,4-6 |
| Challenger Parma | 2023/06/19 10:00 | Filippo Moroni v Gianmarco Ferrari | 7-6,6-7,6-4 |
| Challenger Parma | 2023/06/18 12:35 | Wilson Leite v Gianmarco Ferrari | 4-6,5-7 |
| 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 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 |