Stadium: Center Court Round: 25 Ground: Clay
| ITF M15 Tabarka | 2019/09/11 08:30 | Giacomo Dambrosi v Andrey Chepelev | 1-6,4-6 |
| ITF M15 Tabarka | 2019/09/09 09:00 | Giacomo Dambrosi v Jeremias Lima-Perez | 6-3,6-3 |
| ITF M25 Trieste | 2019/09/03 16:35 | Giacomo Dambrosi v Sandro Ehrat | 6-7,3-6 |
| ITF M15 Tabarka | 2019/08/26 13:00 | Franco Feitt v Giacomo Dambrosi | 0-6,7-6,11-9 |
| ITF M15 Tabarka | 2019/08/26 08:00 | Lisandru Rodriguez v Giacomo Dambrosi | 5-7,2-6 |
| ITF M15 Tabarka | 2019/08/21 09:40 | Giacomo Dambrosi v Matias Zukas | 4-6,4-6 |
| ITF M15 Tabarka | 2019/08/19 14:30 | Giacomo Dambrosi v Vladislav Ivanov | 6-2,2-6,10-3 |
| ITF M15 Tabarka | 2019/08/17 08:30 | Lorenzo Bocchi v Giacomo Dambrosi | 6-3,6-1 |
| Challenger Szczecin | 2019/09/11 11:10 | Pawel Juszczak v Alessandro Giannessi | 6-2,6-0 |
| Challenger Como | 2019/08/31 12:10 | Facundo Mena v Alessandro Giannessi | 6-2,1-6,6-2 |
| Challenger Como | 2019/08/30 13:20 | Alessandro Giannessi v Dmitry Popko | 7-6,4-6,6-4 |
| Challenger Como | 2019/08/29 13:25 | Alessandro Giannessi v Sebastian Ofner | 6-4,6-2 |
| Challenger Como | 2019/08/28 08:00 | Alessandro Giannessi v Johan Sebastien Tatlot | 1-6,6-4,6-3 |
| US Open | 2019/08/22 16:25 | Constant Lestienne v Alessandro Giannessi | 6-3,6-0 |
| US Open | 2019/08/20 15:00 | Jeffrey John Wolf v Alessandro Giannessi | 6-2,5-7,2-6 |
| Challenger Sopot | 2019/07/30 13:25 | Alessandro Giannessi v Aleksandre Metreveli | 6-4,3-6,4-6 |