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 | Jakub Wojcik v Riccardo Chessari | 7-6,6-2 |
| ITF M25 - Santa Margherita | 2023/04/16 08:00 | Paolo Emilio Cossu Floris v Riccardo Chessari | 1-6,1-6 |
| ITF M15 - Antalya | 2023/03/05 06:30 | Filippo Speziali v Riccardo Chessari | 6-1,6-3 |
| ITF M15 - Antalya | 2023/02/27 12:35 | Vilius Gaubas v Riccardo Chessari | 6-2,6-4 |
| 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 |