Stadium: Center Court Round: 25 Ground: Clay
| ITF M15 Skopje | 2021/06/10 07:30 | Rrezart Cungu v Jacopo Berrettini | 6-2,6-3 |
| Challenger Biella | 2021/06/04 13:45 | Jacopo Berrettini v Marco Trungelliti | 5-7,3-6 |
| Challenger Biella | 2021/06/03 11:30 | Jacopo Berrettini v Ramkumar Ramanathan | 5-7,6-1,6-4 |
| Challenger Biella | 2021/05/31 09:00 | Jacopo Berrettini v Antoine Escoffier | 2-6,6-4,7-5 |
| Challenger Biella | 2021/05/30 09:00 | Nicola Kuhn v Jacopo Berrettini | 4-6,3-6 |
| ITF M15 Antalya | 2021/05/14 08:55 | Jacopo Berrettini v Francesco Forti | 2-6,6-2,1-6 |
| ITF M15 Antalya | 2021/05/13 08:45 | David Pichler v Jacopo Berrettini | 6-7,6-3,4-6 |
| ITF M15 Antalya | 2021/05/12 09:15 | Jacopo Berrettini v Edoardo Eremin | 0-6,6-4,6-2 |
| French Open | 2021/05/30 12:30 | Kei Nishikori v Alessandro Giannessi | 6-4,6-7,6-3,4-6,6-4 |
| French Open | 2021/05/28 11:05 | Francisco Cerundolo v Alessandro Giannessi | 4-6,6-3,2-6 |
| French Open | 2021/05/26 13:10 | Alessandro Giannessi v Tallon Griekspoor | 7-5,7-5 |
| French Open | 2021/05/25 11:25 | Ruben Bemelmans v Alessandro Giannessi | 4-6,7-6,5-7 |
| ATP Lyon | 2021/05/17 08:00 | Alessandro Giannessi v Kamil Majchrzak | 4-6,3-6 |
| ATP Lyon | 2021/05/16 09:40 | Peter Polansky v Alessandro Giannessi | 3-6,4-6 |
| Challenger Heilbronn | 2021/05/12 13:15 | Alessandro Giannessi v Daniel Elahi Galan | 7-6,6-7,4-6 |
| Challenger Heilbronn | 2021/05/10 15:40 | Alessandro Giannessi v Prajnesh Gunneswaran | 7-6,6-1 |