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 - M25 Santa Margherita | 2023/04/17 08:30 | Wojcik, Jakub v Chessari, Riccardo | 7-6,6-2 |
| ITF - M25 Santa Margherita | 2023/04/16 08:00 | Cossu Floris, Paolo Emilio v Chessari, Riccardo | 1-6,1-6 |
| ITF - M15 Antalya | 2023/03/05 06:30 | Filippo Speziali v Chessari, Riccardo | 6-1,6-3 |
| ITF - M15 Antalya | 2023/02/27 12:35 | Vilius Gaubas v Chessari, Riccardo | 6-2,6-4 |
| ITF - M15 Monastir | 2023/02/12 09:30 | Chessari, Riccardo v Andrea Bolla | 6-3,4-6,8-10 |
| ITF - M15 Monastir | 2023/02/08 11:00 | Florent Bax v Chessari, Riccardo | 6-2,6-0 |
| ITF - M15 Monastir | 2023/02/06 09:00 | Dali Blanch v Chessari, Riccardo | 6-4,6-4 |
| ITF - M15 Sharm El Sheikh | 2022/12/04 10:00 | Matthew Summers v Chessari, Riccardo | 7-5,6-0 |