Round: 62 Ground: Clay
| ITF Italy F18 | 2016/06/29 16:10 | Davide Galoppini v Goncalo Oliveira | 4-6,6-4,6-4 |
| ITF Italy F18 | 2016/06/28 15:00 | Federico Ottolini v Goncalo Oliveira | 3-6,3-6 |
| Challenger Milan Qual | 2016/06/19 09:30 | Goncalo Oliveira v Lorenzo Sonego | 1-6,2-6 |
| Challenger Perugia Qual | 2016/06/11 08:30 | Ricardo Rodriguez-Pace v Goncalo Oliveira | 5-7,7-5,7-6 |
| ITF Italy F14 | 2016/06/09 08:00 | Adelchi Virgili v Goncalo Oliveira | 7-6,3-6,6-3 |
| ITF Italy F14 | 2016/06/07 12:30 | Mateo Nicolas Martinez v Goncalo Oliveira | 6-7,2-6 |
| ITF Italy F13 | 2016/05/31 09:30 | Johan Sebastien Tatlot v Goncalo Oliveira | 6-3,6-2 |
| ITF Italy F13 | 2016/05/30 08:00 | Goncalo Oliveira v Riccardo Roberto | 6-1,6-3 |
| ITF Austria F1 | 2016/07/02 07:15 | Johannes Bangratz v Jonas Trinker | 7-6,6-2 |