Stadium: Court 7 Round: 54 Ground: Clay
| ITF M15 Bad Waltersdorf | 2021/08/31 08:20 | Leonardo Taddia v Luca Castagnola | 6-2,4-6,10-6 |
| Challenger Vicenza | 2023/05/28 10:10 | Luca Castagnola v Stefano Travaglia | 2-6,3-6 |
| ITF M15 Warmbad-Villach | 2023/05/23 11:15 | Gilles Arnaud Bailly v Luca Castagnola | 6-4,7-5 |
| ITF M15 Warmbad-Villach | 2023/05/22 11:15 | Luca Castagnola v Federico Marchetti | 3-6,6-3,10-8 |
| ITF M15 Warmbad-Villach | 2023/05/21 08:00 | Luca Castagnola v Luka Miklavcic | 7-6,6-1 |
| ITF - M25 Reggio Emilia | 2023/05/15 15:00 | Luca Castagnola v Louroi Martinez | 6-1,4-6,10-12 |
| ITF - M25 Reggio Emilia | 2023/05/15 08:00 | Luca Castagnola v Patric Prinoth | 6-2,6-1 |
| Challenger - Cagliari | 2023/05/01 11:55 | Gianluca Mager v Luca Castagnola | 6-4,4-6,6-4 |
| ITF - M25 Santa Margherita | 2023/04/24 14:25 | Luca Castagnola v Tommaso Compagnucci | 4-6,5-7 |
| ITF M25 Rome | 2023/05/29 09:30 | Samuele Pieri v Leonardo Taddia | 6-2,6-2 |
| ITF M25 Rome | 2023/05/28 12:30 | Dudun, Igor v Leonardo Taddia | 3-6,3-6 |
| ITF M25 Rome | 2023/05/28 07:00 | Leonardo Taddia v Alessandro Pecci | 7-6,1-6,11-9 |
| ITF - M25 Reggio Emilia | 2023/05/15 09:20 | Pijus Vaitiekunas v Leonardo Taddia | 6-1,6-4 |
| ITF - M25 Santa Margherita | 2023/05/02 08:30 | Leonardo Taddia v Giovanni Oradini | 1-6,5-7 |
| ITF - M25 Santa Margherita | 2023/05/01 08:00 | Leonardo Taddia v Leonardo Malgaroli | 5-7,6-1,11-9 |
| ITF - M25 Santa Margherita | 2023/04/30 08:00 | Leonardo Taddia v Umberto Maria Giovannini | 3-6,7-5,10-6 |
| ITF - M25 Trente | 2023/03/27 12:35 | Daniil Glinka v Leonardo Taddia | 7-5,7-5 |