Stadium: Court 2 Round: 26 Ground: Clay
| ITF M25 Santa Margherita | 2022/05/11 12:50 | Andrea Fiorentini v Riccardo Chessari | 2-6,6-0,3-6 |
| ITF M25 Santa Margherita | 2022/05/10 16:25 | Riccardo Chessari v Rocco Piatti | 7-5,7-6 |
| 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 M25 Santa Margherita | 2022/05/11 14:50 | Andrea Gola v Oliver Crawford | 0-6,2-6 |
| ITF M25 Santa Margherita | 2022/05/05 15:30 | Oliver Crawford v Timo Stodder | 6-7,2-6 |
| ITF M25 Santa Margherita | 2022/05/04 13:45 | Oliver Crawford v Omar Giacalone | 6-3,6-3 |
| ITF M25 Santa Margherita | 2022/05/03 13:10 | Oliver Crawford v Edoardo Zanada | 7-6,6-1 |
| Challenger Savannah | 2022/04/27 20:25 | Oliver Crawford v Jose Pereira | 4-6,3-6 |
| Challenger Savannah | 2022/04/25 19:25 | Oliver Crawford v Learner Tien | 6-3,6-1 |
| ITF M25 Rosario | 2022/04/05 20:40 | Leonardo Aboian v Oliver Crawford | 7-6,6-3 |
| ITF M25 Rosario | 2022/04/02 15:45 | Gonzalo Villanueva v Oliver Crawford | 7-6,6-0 |