Estadio: Quadra 2 Round: 27 Ground: Clay
| Challenger Florianópolis | 2023/04/20 13:00 | Alessandro Giannessi v Pedro Boscardin Dias | 6-4,6-4 |
| Challenger Florianópolis | 2023/04/19 13:00 | Alessandro Giannessi v Juan Bautista Otegui | 6-2,6-3 |
| Challenger de Madrid | 2023/04/09 12:30 | Alessandro Giannessi v David Jorda Sanchis | 6-3,6-7,3-6 |
| ATP Estoril | 2023/04/03 17:50 | Alessandro Giannessi v Fabio Fognini | 2-6,1-6 |
| ATP Estoril | 2023/04/02 11:00 | Fabian Marozsan v Alessandro Giannessi | 6-4,6-7,4-6 |
| ATP Estoril | 2023/04/01 12:15 | Alessandro Giannessi v Oleksii Krutykh | 1-6,7-5,6-1 |
| Challenger de Sanremo | 2023/03/28 10:20 | Giulio Zeppieri v Alessandro Giannessi | 6-1,6-1 |
| Challenger de Zadar | 2023/03/26 10:00 | Sebastian Ofner v Alessandro Giannessi | 4-6,7-5,6-7 |
| Challenger Florianópolis | 2023/04/20 13:00 | Pedro Sakamoto v Benjamin Hassan | 6-4,3-6,2-6 |
| Challenger Florianópolis | 2023/04/18 19:15 | Benjamin Hassan v Luciano Darderi | 5-7,6-4,6-4 |
| Challenger Split | 2023/04/10 10:05 | Nerman Fatic v Benjamin Hassan | 6-4,3-6,6-3 |
| Challenger Split | 2023/04/09 14:00 | Luka Mikrut v Benjamin Hassan | 5-7,6-7 |
| Challenger de Biena | 2023/03/25 12:00 | Benjamin Hassan v Jurij Rodionov | 3-6,5-7 |
| Challenger de Biena | 2023/03/24 11:40 | Benjamin Hassan v Norbert Gombos | 7-6,6-2 |
| Challenger de Biena | 2023/03/22 18:10 | Benjamin Hassan v Thai-Son Kwiatkowski | 6-4,7-6 |
| Challenger de Biena | 2023/03/20 17:10 | Alexander Ritschard v Benjamin Hassan | 6-7,6-4,6-7 |