Stadium: Court 2 Round: 25 Ground: Clay
| ITF - M15 Bergamo | 2023/06/26 15:00 | Samuele Pieri v Bautista Vilicich | 6-2,6-1 |
| ITF - M15 Bergamo | 2023/06/25 19:05 | Samuele Pieri v Gustavo Giudici | 6-1,6-1 |
| ITF - M25 Cattolica | 2023/06/19 18:00 | Samuele Pieri v Carlo Alberto Fossati | 7-6,3-6,2-6 |
| ITF - M15 Chieti | 2023/06/16 17:05 | Andrea Picchione v Samuele Pieri | 6-1,6-2 |
| ITF - M15 Chieti | 2023/06/14 10:10 | Samuele Pieri v Andrea Bolla | 6-2,6-4 |
| ITF - M15 Frascati | 2023/06/06 08:00 | Samuele Pieri v Alessandro Pecci | 5-7,4-6 |
| ITF - M15 Frascati | 2023/06/05 14:00 | Samuele Pieri v Niccolo Ciavarella | 6-3,6-2 |
| ITF - M15 Frascati | 2023/06/04 08:00 | Samuele Pieri v Savelii Shpita | 6-1,6-1 |
| 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 |
| ITF - M25 Kiseljak | 2023/05/31 11:50 | Corey Gaal v Gonzalo Villanueva | 5-7,2-6 |
| Challenger - Skopje | 2023/05/21 09:00 | Gonzalo Villanueva v Mathias Bourgue | 2-6,2-6 |