Stadium: Grandstand Round: 27 Ground: Clay
| Challenger Todi | 2023/08/16 12:00 | Luciano Darderi v Miljan Zekic | 6-4,6-4 |
| Challenger Todi | 2023/08/15 18:50 | Luciano Darderi v Lucas Gerch | 6-2,6-3 |
| Challenger Verona | 2023/07/28 11:00 | Luciano Darderi v Vit Kopriva | 6-4,1-6,0-6 |
| Challenger Verona | 2023/07/27 09:00 | Edoardo Lavagno v Luciano Darderi | 4-6,3-6 |
| Challenger Verona | 2023/07/24 19:00 | Luciano Darderi v Nick Hardt | 6-4,6-0 |
| Challenger Trieste | 2023/07/18 15:40 | Luciano Darderi v Francesco Passaro | 4-6,4-6 |
| Challenger San Benedetto | 2023/07/14 17:20 | Benoit Paire v Luciano Darderi | 6-4,7-6 |
| Challenger San Benedetto | 2023/07/13 15:00 | Luciano Darderi v Albert Ramos-Vinolas | 6-2,4-6,6-4 |
| Challenger Todi | 2023/08/16 10:00 | Carlos Sanchez Jover v Duje Ajdukovic | 6-3,7-5 |
| Challenger Todi | 2023/08/15 10:50 | Carlos Sanchez Jover v Fabrizio Andaloro | 7-6,6-2 |
| Challenger Todi | 2023/08/14 09:00 | Carlos Sanchez Jover v Gian M Di Natale | 6-3,6-4 |
| Challenger Todi | 2023/08/13 09:00 | Carlos Sanchez Jover v Facundo Juarez | 6-4,6-2 |
| Challenger Cordenons | 2023/08/11 17:30 | Riccardo Bonadio v Carlos Sanchez Jover | 7-5,6-3 |
| Challenger Cordenons | 2023/08/09 10:40 | Carlos Sanchez Jover v Nicholas David Ionel | 1-6,6-0,6-2 |
| Challenger Cordenons | 2023/08/08 10:25 | Fausto Tabacco v Carlos Sanchez Jover | 1-6,7-5,4-6 |
| Challenger Trieste | 2023/07/18 15:15 | Carlos Sanchez Jover v Marcello Serafini | 5-7,6-1,6-7 |