Stadium: Court 3 Round: 25 Ground: Clay
| ITF Italy F12 | 2018/06/01 16:20 | Andrea Guerrieri v Jacopo Berrettini | 1-6,2-6 |
| ITF M25 Trieste | 2019/09/03 11:25 | Andrea Guerrieri v Yuta Shimizu | 6-7,6-4,1-6 |
| ITF M25 Trieste | 2019/09/02 07:30 | Andrea Guerrieri v Leonardo Taddia | 6-1,6-3 |
| ITF M15 Santa Cristina | 2019/08/15 08:00 | Pietro Rondoni v Andrea Guerrieri | 6-0,6-4 |
| ITF M15 Santa Cristina | 2019/08/14 11:55 | Patric Prinoth v Andrea Guerrieri | 1-6,1-6 |
| ITF M25 Appiano | 2019/08/10 09:30 | Christian Lindell v Andrea Guerrieri | 7-5,6-2 |
| ITF M25 Appiano | 2019/08/09 11:30 | Andrea Guerrieri v Davide Galoppini | 6-2,3-6,7-6 |
| ITF M25 Appiano | 2019/08/08 12:45 | Andrea Guerrieri v Giuseppe La Vela | 6-0,6-4 |
| ITF M25 Appiano | 2019/08/07 12:15 | Alen Avidzba v Andrea Guerrieri | 3-6,5-7 |
| ITF M25 Santa Margherita | 2019/09/19 12:00 | Matteo Gigante v Jacopo Berrettini | 6-2,7-5 |
| ITF M25 Santa Margherita | 2019/09/18 17:25 | Petro Orlando Fellin v Jacopo Berrettini | 3-6,4-6 |
| Challenger Banja Luka | 2019/09/09 12:45 | Danylo Kalenichenko v Jacopo Berrettini | 6-3,6-1 |
| ITF M25 Trieste | 2019/09/03 11:00 | Jacopo Berrettini v Christian Lindell | 2-6,4-6 |
| ITF M25 Poznan | 2019/08/22 09:00 | Jacopo Berrettini v Camilo Ugo Carabelli | 1-6,1-6 |
| ITF M25 Poznan | 2019/08/21 10:00 | Jacopo Berrettini v Mikolaj Szmyrgala | 6-4,7-6 |
| Challenger Cordenons | 2019/08/12 13:30 | Jacopo Berrettini v Enrico Dalla Valle | 4-6,4-6 |
| Challenger Manerbio | 2019/08/06 09:30 | Jacopo Berrettini v Teymuraz Gabashvili | 0-6,7-6,3-6 |