Stadium: Quadra 3 Round: 26 Ground: Clay
| Challenger Tigre | 2023/01/11 19:05 | Pedro Boscardin Dias v Alessandro Giannessi | 2-6,2-6 |
| Challenger Florianopolis | 2023/04/19 13:00 | Alessandro Giannessi v Juan Bautista Otegui | 6-2,6-3 |
| Challenger 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 Sanremo | 2023/03/28 10:20 | Giulio Zeppieri v Alessandro Giannessi | 6-1,6-1 |
| Challenger Zadar | 2023/03/26 10:00 | Sebastian Ofner v Alessandro Giannessi | 4-6,7-5,6-7 |
| Challenger Zadar | 2023/03/25 12:00 | Alessandro Giannessi v Arthur Cazaux | 6-3,6-4 |
| Challenger Florianopolis | 2023/04/19 14:25 | Pedro Boscardin Dias v Maxime Janvier | 6-4,6-2 |
| UTR Pro Tigre | 2023/04/02 16:04 | Pedro Boscardin Dias v Franco Emanuel Egea | 5-7,6-6 |
| UTR Pro Tigre | 2023/04/01 18:30 | Pedro Boscardin Dias v Joaquin Aguillar Cardozo | 6-2,6-4 |
| UTR Pro Tigre | 2023/03/30 12:00 | Pedro Boscardin Dias v Federico Juan Aguilar | 6-3,6-2 |
| UTR Pro Tigre | 2023/03/29 13:30 | Pedro Boscardin Dias v Guido Ivan Justo | 7-6,6-3 |
| UTR Pro Tigre | 2023/03/28 12:00 | Pedro Boscardin Dias v Ramiro Amarilla | 6-1,6-2 |
| UTR Pro Tigre | 2023/03/27 12:00 | Pedro Boscardin Dias v Lorenzo Gagliardo | 3-6,6-0,6-2 |
| Challenger Vina del Mar | 2023/03/12 18:45 | Pedro Boscardin Dias v Tristan Boyer | 3-6,3-6 |