Stadium: Court 6 Round: 54 Ground: Clay
| Challenger Napoli | 2021/10/11 09:00 | Mariano Tammaro v Jonas Forejtek | 6-3,3-6,2-6 |
| ITF M15 Monastir | 2023/02/12 09:30 | Riccardo Chessari v Andrea Bolla | 6-3,4-6,8-10 |
| ITF M15 Monastir | 2023/02/08 11:00 | Florent Bax v Riccardo Chessari | 6-2,6-0 |
| ITF M15 Monastir | 2023/02/06 09:00 | Dali Blanch v Riccardo Chessari | 6-4,6-4 |
| ITF M15 Sharm El Sheikh | 2022/12/04 10:00 | Matthew Summers v Riccardo Chessari | 7-5,6-0 |
| ITF M15 Sharm El Sheikh | 2022/11/27 08:00 | Riccardo Chessari v Saveliy Ivanov | 7-6,6-3 |
| ITF M25 Santa Margherita | 2022/09/18 15:00 | Riccardo Chessari v Freddie Ridout | 6-4,1-6,6-10 |
| ITF M15 Salerno | 2022/09/05 07:00 | Riccardo Chessari v Vito Dell'Elba | 6-0,3-6,7-10 |
| ITF M15 Salerno | 2022/09/04 09:00 | Riccardo Chessari v Claudio Cataldi | 6-0,6-0 |