Stadium: Court Belem Round: 25 Ground: Clay
| Challenger Braga | 2023/09/29 12:00 | Benjamin Hassan v Pablo Llamas Ruiz | 7-6,6-0 |
| Challenger Braga | 2023/09/28 09:00 | Carlos Sanchez Jover v Pablo Llamas Ruiz | 0-6,1-6 |
| Challenger Braga | 2023/09/26 15:05 | Riccardo Bonadio v Pablo Llamas Ruiz | 1-6,2-6 |
| Challenger Seville | 2023/09/07 14:30 | Pablo Llamas Ruiz v Calvin Hemery | 2-6,6-2,3-6 |
| Challenger Seville | 2023/09/06 14:05 | Pablo Llamas Ruiz v Nikolas Sanchez Izquierdo | 6-7,6-4,6-4 |
| Challenger Seville | 2023/09/05 09:00 | Pablo Llamas Ruiz v Federico Delbonis | 6-4,7-6 |
| US Open | 2023/08/24 15:50 | Pablo Llamas Ruiz v Dominic Stephan Stricker | 7-6,4-6,6-7 |
| US Open | 2023/08/22 16:40 | Pablo Llamas Ruiz v Andrea Collarini | 6-3,6-3 |
| Challenger Braga | 2023/09/27 12:55 | Duje Ajdukovic v Alessandro Giannessi | 7-5,5-7,6-2 |
| Challenger Braga | 2023/09/26 14:00 | Gastao Elias v Alessandro Giannessi | 6-7,4-6 |
| Challenger Seville | 2023/09/07 19:00 | Alessandro Giannessi v Hugo Gaston | 6-3,1-6,0-6 |
| Challenger Seville | 2023/09/06 09:00 | Alessandro Giannessi v Daniel Rincon | 7-6,6-0 |
| Challenger Seville | 2023/09/04 19:50 | Jaume Munar v Alessandro Giannessi | 7-6,3-6,4-6 |
| Challenger Como | 2023/08/31 10:30 | Alessandro Giannessi v Rudolf Molleker | 3-6,1-6 |
| Challenger Como | 2023/08/29 09:00 | Jelle Sels v Alessandro Giannessi | 2-6,2-6 |
| US Open | 2023/08/24 14:00 | Alessandro Giannessi v Giulio Zeppieri | 3-6,4-6 |