Stadium: Grand Stand Round: 26 Ground: Clay
| Challenger Parma | 2019/06/18 08:00 | Taro Daniel v Jacob Grills | 6-4,3-6,4-6 |
| Challenger Parma | 2019/06/17 09:10 | Christopher Heyman v Jacob Grills | 6-7,1-6 |
| ITF M15 Kaltenkirchen | 2019/06/12 13:45 | Jacob Grills v Cedrik-Marcel Stebe | 4-6,6-4,1-6 |
| ITF M15 Kaltenkirchen | 2019/06/11 17:25 | Jacob Grills v Matheus Pucinelli De Almeida | 5-7,7-6,7-6 |
| Challenger Poznan | 2019/06/03 09:55 | Jacob Grills v Zdenek Kolar | 1-6,3-6 |
| ITF M25 Most | 2019/05/30 10:25 | Ondrej Krstev v Jacob Grills | 2-6,6-4,6-3 |
| ITF M25 Most | 2019/05/29 08:00 | Jiri Barnat v Jacob Grills | 3-6,2-6 |
| ITF M25 Jablonec Nad Nisou | 2019/05/23 11:30 | Patrik Rikl v Jacob Grills | 6-1,2-6,6-3 |
| Challenger Parma | 2019/06/18 14:45 | Jacopo Berrettini v Danilo Petrovic | 6-4,7-5 |
| Challenger Parma | 2019/06/17 17:20 | Jacopo Berrettini v Lorenzo Musetti | 6-4,7-5 |
| Challenger Poznan | 2019/06/04 09:30 | Jacopo Berrettini v Tommy Robredo | 2-6,7-6,1-6 |
| Challenger Poznan | 2019/06/03 08:00 | Tobias Simon 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 |