Stadium: Grand Stand Round: 26 Ground: Clay
| Parma II, Italy | 2019/06/18 08:00 | Taro Daniel v Grills, Jacob | 6-4,3-6,4-6 |
| Parma II, Italy | 2019/06/17 09:10 | Heyman, Christopher v Grills, Jacob | 6-7,1-6 |
| Kaltenkirchen, Singles Qualifying M-ITF-GER-05A | 2019/06/12 13:45 | Grills, Jacob v Stebe, Cedrik-Marcel | 4-6,6-4,1-6 |
| Kaltenkirchen, Singles Qualifying M-ITF-GER-05A | 2019/06/11 17:25 | Grills, Jacob v Matheus P De Almeida | 5-7,7-6,7-6 |
| Poznan, Poland | 2019/06/03 09:55 | Grills, Jacob v Zdenek Kolar | 1-6,3-6 |
| ITF M25 Most | 2019/05/30 10:25 | Krstev, Ondrej v Grills, Jacob | 2-6,6-4,6-3 |
| ITF M25 Most | 2019/05/29 08:00 | Jiri Barnat v Grills, Jacob | 3-6,2-6 |
| ITF M25 Jablonec Nad Nisou | 2019/05/23 11:30 | Rikl, Patrik v Grills, Jacob | 6-1,2-6,6-3 |
| Parma II, Italy | 2019/06/18 14:45 | Jacopo Berrettini v Petrovic, Danilo | 6-4,7-5 |
| Parma II, Italy | 2019/06/17 17:20 | Jacopo Berrettini v Lorenzo Musetti | 6-4,7-5 |
| Poznan, Poland | 2019/06/04 09:30 | Jacopo Berrettini v Robredo, Tommy | 2-6,7-6,1-6 |
| Poznan, Poland | 2019/06/03 08:00 | Simon, Tobias v Jacopo Berrettini | 2-6,4-6 |
| Challenger Vicenza | 2019/05/28 09:30 | Benjamin Hassan v Jacopo Berrettini | 6-4,6-7,6-3 |
| ITF M25 Vic | 2019/05/25 09:00 | Jacopo Berrettini v Raul Brancaccio | 5-7,3-6 |
| ITF M25 Vic | 2019/05/23 12:25 | Jacopo Berrettini v Alexander Weis | 6-4,6-0 |
| ITF M25 Vic | 2019/05/22 13:30 | Jacopo Berrettini v Felipe Meligeni Rodrigues Alves | 6-4,6-2 |