Stadium: Court 3 Round: 54 Ground: Clay
| Challenger Trieste | 2022/07/17 10:45 | Luca Castagnola v Giovanni Oradini | 3-6,2-6 |
| ITF M25 Telfs | 2022/07/13 14:30 | Ergi Kirkin v Luca Castagnola | 6-2,6-2 |
| ITF M25 Telfs | 2022/07/11 13:00 | Jeffrey Von Der Schulenburg v Luca Castagnola | 4-6,2-6 |
| ITF M25 Telfs | 2022/07/11 07:30 | Tomas Lanik v Luca Castagnola | 1-6,3-6 |
| ITF M25 Casinalbo | 2022/07/06 10:00 | Moez Echargui v Luca Castagnola | 6-4,6-7,6-1 |
| ITF M25 Casinalbo | 2022/07/05 11:25 | Daniele Capecchi v Luca Castagnola | 5-7,5-7 |
| ITF M25 Casinalbo | 2022/07/04 09:20 | Lorenzo Vatteroni v Luca Castagnola | 0-6,2-6 |
| ITF M25 Casinalbo | 2022/07/03 12:50 | Patric Prinoth v Luca Castagnola | 2-6,3-6 |
| ITF M15 Selva Gardena | 2021/10/24 07:30 | Leonardo Chiari v Federico Salomone | 3-6,2-6 |
| ITF M15 Bad Waltersdorf | 2021/08/29 07:00 | Leonardo Chiari v Kris Krawcewicz | 3-6,1-6 |
| ITF M15 Warmbad-Villach | 2021/08/16 12:30 | Leonardo Chiari v Ondrej Horak | 3-6,2-6 |
| ITF M25 Bolzano | 2021/08/02 09:15 | Leonardo Chiari v Federico Marchetti | 1-6,3-6 |
| ITF M25 Casinalbo | 2021/07/04 11:45 | Leonardo Chiari v Alessandro Ragazzi | 1-6,2-6 |
| ITF M15 Sharm El Sheikh | 2020/03/09 08:00 | Volodymyr Uzhylovskyi v Leonardo Chiari | 6-1,6-3 |
| ITF M15 Sharm El Sheikh | 2020/03/02 08:00 | Leonardo Chiari v Volodymyr Uzhylovskyi | 0-6,0-6 |
| ITF M15 Monastir | 2020/02/17 08:30 | Leonardo Chiari v Sai K R Ganta | 4-6,3-6 |