Stadium: Court Belem Round: 19 Ground: Clay
| Challenger Lisbon | 2023/10/01 09:00 | Henri Squire v Connor Thomson | 6-4,3-6,6-1 |
| Challenger Braga | 2023/09/24 12:15 | Henri Squire v Tiago Pereira | 3-6,6-3,1-6 |
| Challenger Bad Waltersdorf | 2023/09/19 13:10 | Raul Brancaccio v Henri Squire | 7-6,5-7,6-2 |
| Challenger Bad Waltersdorf | 2023/09/18 08:00 | Henri Squire v Marcello Serafini | 6-4,6-2 |
| Challenger Bad Waltersdorf | 2023/09/17 08:00 | Henri Squire v David Pichler | 6-7,6-3,6-4 |
| Challenger Szczecin | 2023/09/12 17:30 | Federico Coria v Henri Squire | 6-4,2-6,6-4 |
| Challenger Szczecin | 2023/09/11 11:40 | Timo Stodder v Henri Squire | 6-7,2-6 |
| Challenger Szczecin | 2023/09/10 12:20 | Jasza Szajrych v Henri Squire | 3-6,4-6 |
| Challenger Lisbon | 2023/10/01 09:00 | Sebastian Fanselow v Francesco Forti | 4-6,1-6 |
| ITF M25 Santa Margherita | 2023/09/27 08:30 | Francesco Forti v Fabrizio Andaloro | 2-6,2-6 |
| ITF M25 Santa Margherita | 2023/09/26 10:10 | Francesco Forti v Kirill Mishkin | 6-1,6-0 |
| ITF M25 Pozzuoli | 2023/09/17 08:30 | Arthur Fery v Francesco Forti | 4-6,3-6 |
| ITF M25 Pozzuoli | 2023/09/16 10:30 | Francesco Forti v Giovanni Oradini | 6-3,6-2 |
| ITF M25 Pozzuoli | 2023/09/15 10:05 | Niccolo Catini v Francesco Forti | 3-6,3-6 |
| ITF M25 Pozzuoli | 2023/09/14 11:00 | Gabriele Vulpitta v Francesco Forti | 3-6,0-6 |
| ITF M25 Pozzuoli | 2023/09/13 08:30 | Marco De Rossi v Francesco Forti | 7-6,6-7,5-7 |