| ITF M15 Alkmaar | 06/26 13:20 | 29 | Jacopo Berrettini v Daniel Rincon | 5-7,1-6 | |
| ITF M15 Alkmaar | 06/25 12:00 | 28 | Michiel de Krom v Jacopo Berrettini | 6-7,2-6 | |
| ITF M15 Alkmaar | 06/24 16:00 | 27 | Luigi Sorrentino v Jacopo Berrettini | 5-7,6-3,2-6 | |
| ITF M15 Alkmaar | 06/23 09:00 | 26 | Jarno Jans v Jacopo Berrettini | 2-6,3-6 | |
| ITF M15 Alkmaar | 06/22 10:35 | 25 | Sidane Pontjodikromo v Jacopo Berrettini | 6-2,5-7,2-6 | |
| ITF M25 Meitar | 11/05 10:50 | 28 | [367] Yshai Oliel v Jacopo Berrettini [455] | Retired | |
| ITF M25 Meitar | 11/04 09:00 | 27 | [455] Jacopo Berrettini v Dan Added [472] | 6-4,2-6,6-2 | |
| ITF M25 Meitar | 11/03 08:00 | 26 | Jacopo Berrettini v Daniel Cukierman | 6-7,6-2,7-6 | |
| ITF M25 Meitar | 11/02 09:40 | 25 | Jacopo Berrettini v Orel Kimhi | 7-6,6-2 | |
| ITF M25 Portimao | 10/27 09:00 | 25 | Jacopo Berrettini v Luis Faria | 6-4,3-6,4-6 | |
| Challenger Napoli | 10/11 12:20 | 25 | [453] Jacopo Berrettini v Manuel Guinard [275] | 5-7,7-6,4-6 | |
| Challenger Napoli | 10/05 13:05 | 25 | [453] Jacopo Berrettini v Andrea Pellegrino [228] | 2-6,4-6 | |
| Challenger Lisbon | 09/28 10:45 | 25 | [160] Cedrik-Marcel Stebe v Jacopo Berrettini [442] | 6-0,6-1 | |
| Challenger Lisbon | 09/27 09:00 | 19 | [442] Jacopo Berrettini v Sebastian Fanselow [423] | 6-4,5-7,2-6 | |
| Challenger Lisbon | 09/26 09:00 | 14 | [384] Alessandro Bega v Jacopo Berrettini [444] | 2-6,4-6 | |
| Challenger Braga | 09/19 11:00 | 14 | [363] Kaichi Uchida v Jacopo Berrettini [441] | 4-6,6-4,7-6 | |
| ITF M25 Madrid | 09/15 08:55 | 25 | Jacopo Berrettini v Carlos L-Montagud | 4-6,6-4,2-6 | |
| Challenger Kyiv | 09/05 12:40 | 14 | [494] Clement Tabur v Jacopo Berrettini [447] | 6-2,6-1 | |
| ITF M25 Sierre | 09/03 14:55 | 27 | Patrick Kypson v Jacopo Berrettini | 7-6,6-7,7-5 | |
| ITF M25 Sierre | 09/02 12:40 | 26 | Emiliano Maggioli v Jacopo Berrettini | 6-7,6-2,2-6 | |
| ITF M25 Sierre | 08/31 10:40 | 25 | Christian Kuehne v Jacopo Berrettini | 3-6,0-6 | |
| Challenger Barletta | 08/23 18:00 | 25 | [122] Andrej Martin v Jacopo Berrettini [445] | 4-6,6-2,6-1 | |
| ITF M25 Muttenz | 08/18 14:35 | 25 | Jacopo Berrettini v Tristan Schoolkate | 1-6,4-6 | |
| ITF M25 Casinalbo | 07/06 11:30 | 25 | Jacopo Berrettini v Riccardo Balzerani | Cancelled | |
| Challenger Milan | 06/20 10:30 | 14 | [295] Evan Furness v Jacopo Berrettini [467] | 7-5,7-6 | |
| Challenger Forli | 06/17 11:20 | 27 | [246] Mats Moraing v Jacopo Berrettini [467] | 6-3,6-4 | |
| Challenger Forli | 06/16 11:25 | 26 | [277] Pedro Cachin v Jacopo Berrettini [467] | 6-7,7-6,4-6 | |
| Challenger Forli | 06/15 16:05 | 25 | [467] Jacopo Berrettini v Alessandro Giannessi [162] | 6-1,7-6 | |
| ITF M15 Szkopje | 06/10 07:30 | 25 | Rrezart Cungu v Jacopo Berrettini | 6-2,6-3 | |
| Challenger Biella | 06/04 13:45 | 27 | [302] Jacopo Berrettini v Marco Trungelliti [237] | 5-7,3-6 |