Estadio: CT Dolomia Serena Round: 24 Ground: Clay
| ITF Italia F14 | 2018/06/13 12:35 | Enrico Dalla Valle v Jacopo Berrettini | 2-6,3-6 |
| Challenger Manerbio | 2019/08/06 09:30 | Jacopo Berrettini v Teymuraz Gabashvili | 0-6,7-6,3-6 |
| Challenger de Sopot | 2019/07/29 11:25 | Ivan Gakhov v Jacopo Berrettini | 6-3,7-5 |
| ITF M25 Arlon | 2019/06/27 08:00 | Jacopo Berrettini v Jeroen Vanneste | 1-6,4-6 |
| ITF M25 Arlon | 2019/06/26 09:40 | Jacopo Berrettini v Sebastian Baez | 6-4,3-6,7-6 |
| Challenger de Parma | 2019/06/21 09:00 | Jacopo Berrettini v Julian Lenz | 1-6,3-6 |
| Challenger de Parma | 2019/06/20 08:00 | Jacob Grills v Jacopo Berrettini | 1-6,4-6 |
| Challenger de Parma | 2019/06/18 14:45 | Jacopo Berrettini v Danilo Petrovic | 6-4,7-5 |
| Challenger de Parma | 2019/06/17 17:20 | Jacopo Berrettini v Lorenzo Musetti | 6-4,7-5 |
| Challenger Manerbio | 2019/08/05 11:45 | Enrico Dalla Valle v Chun Hsin Tseng | 6-7,4-6 |
| Challenger de Sopot | 2019/07/30 08:00 | Christopher O'Connell v Enrico Dalla Valle | 6-0,6-2 |
| ITF M25 Pontedera | 2019/07/28 14:00 | Enrico Dalla Valle v Giulio Zeppieri | 7-6,7-5 |
| ITF M25 Pontedera | 2019/07/27 10:00 | Gonzalo Villanueva v Enrico Dalla Valle | 6-7,1-6 |
| ITF M25 Pontedera | 2019/07/25 16:30 | Marco Miceli v Enrico Dalla Valle | 3-6,2-6 |
| ITF M25 Pontedera | 2019/07/24 12:40 | Lorenzo Bocchi v Enrico Dalla Valle | 6-7,0-6 |
| ITF M15 Tabarka | 2019/07/21 09:00 | Enrico Dalla Valle v Sebastian Baez | 3-6,6-4,6-4 |
| ITF M15 Tabarka | 2019/07/20 09:00 | Enrico Dalla Valle v Nicolas Alberto Arreche | 6-3,6-2 |