Stadium: Court 3 Round: 26 Ground: Clay
| ITF M25 Santa Margherita | 2019/10/04 12:00 | Jacopo Berrettini v Emiliano Maggioli | 4-6,4-6 |
| ITF M25 Sierre | 2021/08/31 10:50 | Emiliano Maggioli v Jesse Flores | 6-1,6-0 |
| Challenger Barletta | 2021/08/23 14:05 | Tim Van Rijthoven v Emiliano Maggioli | 7-5,6-4 |
| ITF M15 Pescara | 2021/08/21 12:55 | Alexis Gautier v Emiliano Maggioli | 6-2,6-1 |
| ITF M15 Pescara | 2021/08/20 10:15 | Giorgio Tabacco v Emiliano Maggioli | 0-6,2-6 |
| ITF M15 Pescara | 2021/08/19 09:30 | Stefano Battaglino v Emiliano Maggioli | 6-4,6-7,2-6 |
| ITF M15 Pescara | 2021/08/18 08:45 | Giovanni Oradini v Emiliano Maggioli | 3-6,4-6 |
| ITF M25 Bolzano | 2021/08/04 07:00 | Raul Brancaccio v Emiliano Maggioli | 4-6,6-0,6-0 |
| ITF M25 Bolzano | 2021/08/03 16:15 | Emiliano Maggioli v Kirill Kivattsev | 1-6,6-4,6-4 |
| ITF M25 Sierre | 2021/08/31 10:40 | Christian Kuehne v Jacopo Berrettini | 3-6,0-6 |
| Challenger Barletta | 2021/08/23 18:00 | Andrej Martin v Jacopo Berrettini | 4-6,6-2,6-1 |
| ITF M25 Muttenz | 2021/08/18 14:35 | Jacopo Berrettini v Tristan Schoolkate | 1-6,4-6 |
| Challenger Milan | 2021/06/20 10:30 | Evan Furness v Jacopo Berrettini | 7-5,7-6 |
| Challenger Forli | 2021/06/17 11:20 | Mats Moraing v Jacopo Berrettini | 6-3,6-4 |
| Challenger Forli | 2021/06/16 11:25 | Pedro Cachin v Jacopo Berrettini | 6-7,7-6,4-6 |
| Challenger Forli | 2021/06/15 16:05 | Jacopo Berrettini v Alessandro Giannessi | 6-1,7-6 |
| ITF M15 Skopje | 2021/06/10 07:30 | Rrezart Cungu v Jacopo Berrettini | 6-2,6-3 |