Stadium: Court 4 Round: 62 Ground: Hardcourt outdoor
| ITF M25 Ueberlingen | 2021/08/16 09:40 | Benito Sanchez Martinez v Thibaut Gadilhe | 5-7,6-0,10-5 |
| 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 |
| ITF M15 Monastir | 2021/05/17 09:00 | Riccardo Chessari v Perry Gregg | 3-6,4-6 |
| ITF M15 Monastir | 2021/05/16 11:00 | Mhamed Affes v Riccardo Chessari | 4-6,1-6 |
| ITF M15 Monastir | 2021/05/10 08:00 | Riccardo Chessari v Uisung Park | 1-6,2-6 |
| ITF M15 Monastir | 2021/05/09 08:00 | Giovanni Agostinetto v Riccardo Chessari | 6-7,0-6 |