Stadium: Center Court Round: 25 Ground: Clay
| 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 |
| ATP - Rím | 2019/05/11 15:25 | Taylor Fritz v Jacopo Berrettini | 6-4,6-3 |
| Challenger - Prostějov | 2019/06/02 13:45 | Danilo Petrovic v Arthur Rinderknech | 4-6,4-6 |
| Challenger Jerusalem | 2019/05/26 14:00 | Danilo Petrovic v Filip Peliwo | 7-6,6-7,6-1 |
| Challenger Jerusalem | 2019/05/25 08:20 | Brayden Schnur v Danilo Petrovic | 3-6,2-6 |
| Challenger Jerusalem | 2019/05/24 09:00 | Danilo Petrovic v Viktor Durasovic | 7-5,6-3 |
| Challenger Jerusalem | 2019/05/23 09:30 | Danilo Petrovic v Emil Ruusuvuori | 6-3,6-4 |
| Challenger Jerusalem | 2019/05/22 12:30 | Dudi Sela v Danilo Petrovic | 3-6,6-7 |
| Challenger Jerusalem | 2019/05/20 08:20 | Ben Patael v Danilo Petrovic | 4-6,4-6 |
| Challenger - Rím | 2019/05/07 10:50 | Hernan Casanova v Danilo Petrovic | 6-4,4-6,6-2 |