Stadium: Campo 2 Round: 14 Ground: Clay
| ITF M25 Biella | 2023/07/06 15:35 | Luca Castagnola v Maxime Chazal | 6-7,2-6 |
| ITF M25 Biella | 2023/07/05 08:55 | Fernando Yamacita v Luca Castagnola | 6-3,2-6,1-6 |
| ITF M25 Biella | 2023/07/04 15:50 | Luca Castagnola v Andrea Bolla | 7-6,7-5 |
| ITF M15 Bergamo | 2023/06/28 11:10 | Luca Castagnola v Niccolo Catini | 2-6,4-6 |
| Challenger Parma | 2023/06/18 10:25 | Luca Castagnola v Sandro Kopp | 4-6,2-6 |
| ITF M15 Chieti | 2023/06/16 11:30 | Luca Castagnola v Manuel Mazza | 4-6,7-5,2-6 |
| ITF M15 Chieti | 2023/06/14 12:50 | Oleksandr Ovcharenko v Luca Castagnola | 3-6,4-6 |
| ITF M15 Frascati | 2023/06/08 10:25 | Enrico Dalla Valle v Luca Castagnola | 6-4,6-3 |
| Challenger Troyes | 2023/07/02 13:30 | Gonzalo Villanueva v Valerio Aboian | 0-6,4-6 |
| ITF M15 Bergamo | 2023/06/27 11:15 | Samuele Pieri v Gonzalo Villanueva | 6-1,6-4 |
| Challenger Parma | 2023/06/18 13:40 | Maxime Janvier v Gonzalo Villanueva | 6-3,6-4 |
| Challenger Perugia | 2023/06/11 08:00 | Nino Serdarusic v Gonzalo Villanueva | 4-6,7-5,6-3 |
| ITF M25 Kursumlijska Banja | 2023/06/08 11:05 | Sebastian Gima v Gonzalo Villanueva | 2-6,6-4,6-1 |
| ITF M25 Kursumlijska Banja | 2023/06/07 10:05 | Aleksei Khomich v Gonzalo Villanueva | 5-7,3-6 |
| ITF M25 Kiseljak | 2023/06/02 10:45 | Pedro Boscardin Dias v Gonzalo Villanueva | 6-1,6-4 |
| ITF M25 Kiseljak | 2023/06/01 08:55 | Samuel Puskar v Gonzalo Villanueva | 3-6,4-6 |