Stadium: Court 5 Round: 54 Ground: Clay
| ITF M25 Santa Margherita | 2022/05/01 14:00 | Federico Marchetti v Riccardo Chessari | 6-7,6-1,10-7 |
| ITF M15 Monastir | 2021/11/03 12:30 | Riccardo Chessari v Omar Giacalone | 2-6,6-4,2-6 |
| ITF M15 Monastir | 2021/10/24 11:00 | Riccardo Chessari v Giannicola Misasi | 4-6,5-7 |
| ITF M15 Monastir | 2021/10/18 09:30 | Thibaut Gadilhe v Riccardo Chessari | 7-5,6-2 |
| ITF M15 Monastir | 2021/10/17 08:00 | Riccardo Chessari v Ethan Terblanche | 6-3,6-4 |
| ITF M15 Monastir | 2021/08/29 08:00 | Riccardo Chessari v Linghao Zhang | 6-7,4-6 |
| ITF M15 Monastir | 2021/08/23 09:00 | Li Tu v Riccardo Chessari | 6-1,6-1 |
| ITF M15 Monastir | 2021/08/22 10:00 | Riccardo Chessari v Dylan Salton | 2-6,6-2,11-9 |