Stadium: Court 7 Round: 19 Ground: Clay
| ITF - M25 Santa Margherita | 2023/10/22 08:00 | Denis Constantin Spiridon v Colacioppo, Giulio | 6-3,2-6,10-5 |
| ITF - M25 Santa Margherita | 2023/10/18 08:00 | Salvatore Caruso v Denis Constantin Spiridon | 6-3,6-1 |
| ITF - M25 Santa Margherita | 2023/10/17 10:05 | Denis Constantin Spiridon v Nicosia, Giuseppe Mario | 6-0,6-0 |
| ITF - M25 Santa Margherita | 2023/10/16 08:00 | Denis Constantin Spiridon v Loccisano, Benjamin | 7-6,6-3 |
| ITF - M25 Santa Margherita | 2023/10/15 08:00 | Denis Constantin Spiridon v Niccolo Dessi | 6-2,3-6,10-4 |
| ITF - M15 Sharm El Sheikh | 2023/10/09 07:00 | Denis Constantin Spiridon v Cedric Stanke | 3-6,6-4,2-10 |
| ITF - M15 Sharm El Sheikh | 2023/10/04 12:50 | Jacob Bradshaw v Denis Constantin Spiridon | 7-6,6-3 |
| ITF - M15 Monastir | 2023/09/05 08:00 | Denis Constantin Spiridon v Gabriele Volpi | 2-6,4-6 |
| ITF - M25 Santa Margherita | 2023/10/22 08:30 | Pozzi, Davide v Giammarco Gandolfi | 3-6,1-6 |
| ITF - M25 Santa Margherita | 2023/10/10 09:55 | Niccolo Catini v Giammarco Gandolfi | 7-5,6-4 |
| ITF - M25 Santa Margherita | 2023/10/09 07:55 | Perez Sanz, David v Giammarco Gandolfi | 2-6,6-7 |
| ITF - M25 Santa Margherita | 2023/10/03 13:30 | Gianmarco Ferrari v Giammarco Gandolfi | 6-1,7-5 |
| ITF - M25 Santa Margherita | 2023/09/24 08:00 | Giammarco Gandolfi v Dax Donders | 3-6,3-6 |
| Pirot, Singles M-ITF-SRB-05A | 2023/09/06 12:30 | Giammarco Gandolfi v Vlad Andrei Dancu | 3-6,6-3,2-6 |
| Pirot, Singles M-ITF-SRB-05A | 2023/09/05 07:30 | Lazar Vojinovic v Giammarco Gandolfi | 7-6,4-6,3-10 |
| Pirot, Singles M-ITF-SRB-05A | 2023/09/04 10:00 | Egor Khotchenkov v Giammarco Gandolfi | 6-7,3-6 |