Stadium: Center Court Round: 54 Ground: Hardcourt outdoor
| ITF M15 Bergamo | 2023/06/29 18:30 | Luigi Castelletti v Nicolas Parizzia | 6-4,6-7,3-6 |
| ITF M15 Bergamo | 2023/06/28 09:45 | Giulio Colacioppo v Luigi Castelletti | 6-1,4-6,3-6 |
| ITF M25 Cattolica | 2023/06/18 09:00 | Luigi Castelletti v Rushil Khosla | 3-6,6-7 |
| ITF M15 Frascati | 2023/06/04 11:40 | Luigi Castelletti v Mariano Tammaro | 1-6,4-6 |
| ITF M25 Rome | 2023/05/28 07:00 | Luigi Castelletti v Francesco Ferrari | 2-6,2-6 |
| ITF M25 Reggio Emilia | 2023/05/15 14:15 | Kyle Edmund v Luigi Castelletti | 6-3,6-3 |
| ITF M15 Alaminos-Larnaca | 2023/05/09 09:30 | Igor Trunov v Luigi Castelletti | 6-3,6-1 |
| ITF M15 Alaminos-Larnaca | 2023/05/08 07:00 | Luigi Castelletti v Andrea Militi Ribaldi | 7-6,6-4 |