Stadium: Court Central Round: 19 Ground: Hardcourt indoor
| Challenger Oeiras | 2023/05/14 10:25 | Alessandro Giannessi v Alberto Barroso Campos | 6-1,6-3 |
| Challenger Francavilla | 2023/05/10 11:20 | Benoit Paire v Alessandro Giannessi | 7-5,7-5 |
| Challenger Francavilla | 2023/05/09 09:00 | Alessandro Giannessi v Marco Trungelliti | 3-6,6-3,6-4 |
| Challenger Cagliari | 2023/05/04 11:45 | Alessandro Giannessi v Thanasi Kokkinakis | 4-6,2-6 |
| Challenger Cagliari | 2023/05/03 10:25 | Alessandro Giannessi v Francesco Passaro | 3-6,7-6,6-4 |
| Challenger Cagliari | 2023/05/02 08:30 | Alessandro Giannessi v Alexander Erler | 7-5,6-1 |
| Challenger Florianopolis | 2023/04/21 16:15 | Alessandro Giannessi v Benjamin Hassan | 6-3,4-6,6-7 |
| Challenger Florianopolis | 2023/04/20 13:00 | Alessandro Giannessi v Pedro Boscardin Dias | 6-4,6-4 |
| Challenger Oeiras | 2023/05/14 11:00 | Jaime Faria v Daniel Michalski | 6-1,3-6,3-6 |
| ITF M25 Santa Margherita | 2023/05/06 07:55 | Sebastian Fanselow v Daniel Michalski | 1-6,2-6 |
| ITF M25 Santa Margherita | 2023/05/05 07:55 | Lukas Neumayer v Daniel Michalski | 4-6,1-6 |
| ITF M25 Santa Margherita | 2023/05/04 09:55 | Mikalai Haliak v Daniel Michalski | 4-6,4-6 |
| ITF M25 Santa Margherita | 2023/05/03 15:55 | Alessandro Cortegiani v Daniel Michalski | 3-6,2-6 |
| ITF M25 Santa Margherita | 2023/05/02 09:20 | Michele Ribecai v Daniel Michalski | 6-7,0-6 |
| ITF M25 Santa Margherita | 2023/04/15 09:30 | Daniel Michalski v Goncalo Oliveira | 3-6,2-6 |
| ITF M25 Santa Margherita | 2023/04/14 09:45 | Pietro Marino v Daniel Michalski | 2-6,5-7 |