Stadium: Court 2 De Luigi Round: 19 Ground: Clay
| Challenger San Marino | 2023/07/30 08:00 | Kyrian Jacquet v Lorenzo Bocchi | 6-3,6-3 |
| Challenger Zug | 2023/07/24 09:00 | Dylan Dietrich v Kyrian Jacquet | 6-2,5-7,6-4 |
| Challenger Zug | 2023/07/23 10:30 | Andrin Casanova v Kyrian Jacquet | 3-6,1-6 |
| Challenger Trieste | 2023/07/21 12:10 | Kyrian Jacquet v Hugo Gaston | 6-4,4-6,4-6 |
| Challenger Trieste | 2023/07/20 10:00 | Kyrian Jacquet v Vitaliy Sachko | 6-3,6-4 |
| Challenger Trieste | 2023/07/18 09:00 | Kyrian Jacquet v Carlos Taberner | 6-3,7-6 |
| Challenger Trieste | 2023/07/17 09:00 | Kyrian Jacquet v Andrey Chepelev | 6-3,6-4 |
| Challenger Trieste | 2023/07/16 11:30 | Kyrian Jacquet v Aldin Setkic | 6-2,6-1 |
| Challenger San Marino | 2023/07/30 08:00 | Simone Roncalli v Gianmarco Ferrari | 5-7,6-3,0-6 |
| Challenger Zug | 2023/07/25 08:50 | Arthur Rinderknech v Gianmarco Ferrari | 7-6,6-3 |
| Challenger Zug | 2023/07/24 12:10 | Gianmarco Ferrari v Vladyslav Orlov | 6-3,6-4 |
| 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 Milan | 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 |