Stadium: Campo 2 Round: 14 Ground: Clay
| 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 |
| ITF - M25 Reggio Emilia | 2023/05/15 11:05 | Federico Iannaccone v Benito Massacri | 6-2,6-1 |
| ITF - M25 Santa Margherita | 2023/05/03 13:25 | Benito Massacri v Giovanni Oradini | 0-6,4-6 |
| ITF - M25 Santa Margherita | 2023/05/02 08:00 | Benito Massacri v Rocco Piatti | 3-6,6-0,6-4 |
| Challenger Troyes | 2023/07/02 08:00 | Emilien Voisin v Ocleppo, Julian | 6-4,7-6 |
| Challenger Modena | 2023/06/27 10:30 | Ocleppo, Julian v Salvatore Caruso | 4-6,6-3,0-6 |
| Challenger Modena | 2023/06/26 10:30 | Mathias Bourgue v Ocleppo, Julian | 2-6,5-7 |
| Challenger Modena | 2023/06/25 11:20 | Ocleppo, Julian v Duje Ajdukovic | 6-1,7-6 |
| ITF M25 Cattolica | 2023/06/22 12:00 | Gonzalo Bueno v Ocleppo, Julian | 6-0,6-4 |
| ITF M25 Cattolica | 2023/06/21 12:00 | Leopold Zima v Ocleppo, Julian | 6-7,0-6 |
| ITF M25 Cattolica | 2023/06/20 13:05 | Luca Fantini v Ocleppo, Julian | 3-6,4-6 |
| ITF M15 Frascati | 2023/06/11 08:30 | Ocleppo, Julian v Stefano Napolitano | 6-4,7-5 |