Stadium: Center Court Round: 25 Ground: Clay
| Challenger Valencia | 2023/11/22 11:45 | Alessandro Giannessi v Albert Ramos-Vinolas | 1-6,6-0,6-7 |
| Challenger Valencia | 2023/11/21 10:00 | Alessandro Giannessi v Miguel Damas | 6-2,6-4 |
| Challenger Montevideo | 2023/11/14 15:00 | Facundo Diaz Acosta v Alessandro Giannessi | 6-1,7-5 |
| Challenger Lima | 2023/11/08 18:30 | Alessandro Giannessi v Daniel Elahi Galan | 4-6,3-6 |
| Challenger Lima | 2023/11/07 17:45 | Alessandro Giannessi v Oriol Roca Batalla | 1-6,6-3,6-2 |
| Challenger Olbia | 2023/10/17 20:10 | Lloyd Harris v Alessandro Giannessi | 7-6,6-0 |
| Challenger Lisbon | 2023/10/02 14:10 | Pablo Llamas Ruiz v Alessandro Giannessi | 6-3,6-1 |
| Challenger Braga | 2023/09/27 12:55 | Duje Ajdukovic v Alessandro Giannessi | 7-5,5-7,6-2 |
| ITF - Vale Do Lobo M25 | 2023/11/25 11:30 | Khumoyun Sultanov v Henrique Rocha | 6-4,6-2 |
| ITF - Vale Do Lobo M25 | 2023/11/24 12:45 | Henrique Rocha v Leopold Zima | 6-2,7-5 |
| ITF - Vale Do Lobo M25 | 2023/11/23 14:20 | Henrique Rocha v Marco Berti | 6-0,6-1 |
| ITF - Vale Do Lobo M25 | 2023/11/22 13:10 | Henrique Rocha v Diogo Marques | 6-1,6-3 |
| ITF - Vale Do Lobo M25 | 2023/11/19 12:00 | Hynek Barton v Henrique Rocha | 3-6,1-6 |
| ITF - Vale Do Lobo M25 | 2023/11/18 10:55 | Henrique Rocha v Khumoyun Sultanov | 6-4,7-5 |
| ITF - Vale Do Lobo M25 | 2023/11/16 12:00 | Rayane Oumaouche v Henrique Rocha | 2-6,1-6 |
| ITF - Vale Do Lobo M25 | 2023/11/15 12:45 | Rodrigo Fernandes v Henrique Rocha | 0-6,1-6 |