Stadium: Court 1 Round: 54 Ground: Hardcourt outdoor
| ITF M15 Koszalin | 2023/09/03 09:00 | Alexander C Parker v Mattia Ricci | 6-2,2-6,10-7 |
| Challenger Cordenons | 2023/08/06 09:00 | Benito Massacri v Gonzalo Villanueva | 1-6,2-6 |
| ITF M15 Perugia | 2023/07/23 14:00 | Benito Massacri v Peter Buldorini | 3-6,1-6 |
| Challenger San Benedetto | 2023/07/09 09:00 | Benito Massacri v Julian Ocleppo | 2-6,2-6 |
| ITF M15 Chieti | 2023/06/13 09:35 | Giammarco Gandolfi v Benito Massacri | 6-4,6-1 |
| ITF M15 Frascati | 2023/06/05 12:25 | Mert Alkaya v Benito Massacri | 6-3,6-2 |
| ITF M15 Frascati | 2023/06/04 11:45 | Valerio Calisti v Benito Massacri | 0-6,0-6 |
| ITF M25 Rome | 2023/05/28 12:30 | Samuele Pieri v Benito Massacri | 6-0,7-6 |
| ITF M25 Rome | 2023/05/28 07:00 | Benito Massacri v Josh Reid | 6-2,6-1 |