| ITF - M15 Antalya | 02/04 06:20 | 25 | [493] Timur Kiyamov v Jacopo Berrettini [492] | 3-6,6-4,5-7 | |
| ITF - M15 Antalya | 01/30 07:05 | 25 | [492] Jacopo Berrettini v Diego Hidalgo [392] | 4-6,3-6 | |
| ITF - M15 Antalya | 01/29 07:00 | - | Jacopo Berrettini v Maxime Hamou | View | |
| ITF - M15 Monastir | 01/14 09:00 | 26 | Jacopo Berrettini v Martin Breysach | Postponed | |
| ITF - M15 Monastir | 01/13 08:00 | 25 | Jacopo Berrettini v Raphael Collignon | 3-6,6-3,6-4 | |
| ITF - M15 Heraklion | 11/02 11:00 | 44 | Jacopo Berrettini v Federico Arnaboldi | 6-4,5-7,7-10 | |
| ITF - M15 Heraklion | 11/01 12:00 | 44 | Jacopo Berrettini v Tadeas Paroulek | 6-3,6-3 | |
| ITF - M15 Heraklion | 10/30 10:00 | 27 | Fabian Marozsan v Jacopo Berrettini | 7-6,6-4 | |
| ITF - M15 Heraklion | 10/29 08:00 | 26 | [412] Facundo D Acosta v Jacopo Berrettini [486] | 5-7,2-6 | |
| ITF - M15 Heraklion | 10/27 11:25 | 25 | [484] Jacopo Berrettini v Vaclav Safranek [334] | 7-6,6-2 | |
| ITF - M15 Setubal | 10/07 10:55 | 25 | Luis Faria v Jacopo Berrettini | 6-3,6-4 | |
| ITF - M25 Porto | 09/28 13:30 | 44 | Jacopo Berrettini v Mateus Alves | 3-6,6-7,7-10 | |
| ITF - M25 Porto | 09/27 15:00 | 44 | Jacopo Berrettini v Mathys Erhard | 6-3,1-6,11-9 | |
| ITF - M15 Castelo Branco | 09/23 15:00 | 25 | Mark Whitehouse v Jacopo Berrettini | 6-3,6-4 | |
| ATP - Roma | 09/12 12:05 | - | [490] Jacopo Berrettini v Leonardo Mayer [120] | 3-6,2-6 | |
| ITF - M15 Caslano | 09/02 13:00 | 25 | [346] Juan Manuel Cerundolo v Jacopo Berrettini [490] | 6-4,4-6,6-0 | |
| ITF - M15 Alkmaar | 08/30 13:00 | 29 | [323] Igor Sijsling v Jacopo Berrettini [490] | 6-2,6-1 | |
| ITF - M15 Alkmaar | 08/29 13:40 | 28 | Clement Geens v Jacopo Berrettini | Retired | |
| ITF - M15 Alkmaar | 08/28 11:00 | 27 | Jacopo Berrettini v Juan Pablo Paz | 6-2,6-4 | |
| ITF - M15 Alkmaar | 08/27 11:45 | 26 | Jacopo Berrettini v Peter Makk | 7-6,1-6,7-6 | |
| ITF - M15 Alkmaar | 08/25 15:15 | 25 | Jacopo Berrettini v Alexander Weis | 7-6,4-6,6-1 | |
| Challenger - Todi | 08/15 12:15 | 64 | [491] Jacopo Berrettini v Andrea Arnaboldi [282] | 2-6,0-6 | |
| Italia - Umbrian Open | 06/24 17:30 | - | [491] Jacopo Berrettini v Andrea Arnaboldi [282] | 4-6,3-6 | |
| Italia - Umbrian Open | 06/22 11:45 | - | Fabrizio Ornago v Jacopo Berrettini | View | |
| Italia - Umbrian Open | 06/22 10:00 | 1 | [413] Fabrizio Ornago v Jacopo Berrettini [491] | 6-3,4-6,4-10 | |
| ITF - M15 Sharm El Sheikh | 02/22 08:00 | 28 | Robin Stanek v Jacopo Berrettini | 7-5,6-4 | |
| ITF - M15 Sharm El Sheikh | 02/21 08:00 | 27 | Oleksandr Ovcharenko v Jacopo Berrettini | 4-6,4-6 | |
| ITF - M15 Sharm El Sheikh | 02/20 09:40 | 26 | Issei Okamura v Jacopo Berrettini | 1-6,2-6 | |
| ITF - M15 Sharm El Sheikh | 02/19 08:00 | 25 | Simon A Ivanov v Jacopo Berrettini | 5-7,4-6 | |
| ITF - M15 Sharm El Sheikh | 02/14 08:00 | 27 | Egor Agafonov v Jacopo Berrettini | 3-6,6-3,6-4 |