Stadium: Centre Court Round: 64 Ground: Clay
| ATP - Rio De Janeiro | 2019/02/16 18:00 | Londero, Juan Ignacio v Alessandro Giannessi | 7-6,6-1 |
| ATP - Buenos Aires | 2019/02/09 19:00 | Alessandro Giannessi v Marco Trungelliti | 6-4,6-1 |
| ATP - Cordoba | 2019/02/07 23:10 | Diego Schwartzman v Alessandro Giannessi | 6-7,6-3,6-0 |
| ATP - Cordoba | 2019/02/05 18:30 | Alessandro Giannessi v Thiago Seyboth Wild | 6-7,7-5,7-6 |
| ATP - Cordoba | 2019/02/03 20:25 | Lorenzi, Paolo v Alessandro Giannessi | 7-6,4-6,6-7 |
| Challenger - Punta del Este | 2019/01/23 15:40 | Tomas Barrios Vera v Alessandro Giannessi | 6-4,6-4 |
| Open d'Australie | 2019/01/07 23:00 | Alessandro Giannessi v Vanni, Luca | 4-6,4-6 |
| Challenger - Barcelone | 2018/10/12 14:00 | Roberto Carballes Baena v Alessandro Giannessi | 6-2,6-2 |
| Challenger - Morelos | 2019/02/19 17:20 | Souza, Joao Olavo v Quiroz, Roberto | 4-6,0-6 |
| Challenger - Morelos | 2019/02/18 18:05 | Souza, Joao Olavo v Patino, Luis | 6-4,6-3 |
| Challenger Dallas | 2019/02/04 17:40 | Souza, Joao Olavo v Liam Broady | 6-4,6-7,2-6 |
| ITF M25 Weston | 2019/02/02 15:30 | Dmitry Popko v Souza, Joao Olavo | 7-6,6-2 |
| ITF M25 Weston | 2019/01/30 18:00 | Souza, Joao Olavo v Olivares, Jose | 6-4,6-3 |
| Challenger - Punta del Este | 2019/01/22 21:35 | Thiago Monteiro v Souza, Joao Olavo | 7-6,6-2 |
| Challenger - Punta del Este | 2019/01/21 18:50 | Souza, Joao Olavo v Preston Brown | 6-2,6-4 |
| Challenger Columbus | 2019/01/08 16:00 | Souza, Joao Olavo v Goncalo Oliveira | 4-6,1-6 |