Round: 25 Ground: Clay
| ITF Italy F16 Qual | 2016/06/19 09:10 | Carli, Christian v Ottolini, Federico | 6-1,6-3 |
| ITF Italy F16 Qual | 2016/06/18 10:55 | Ottolini, Federico v Curci, Matteo | 6-2,7-6 |
| ITF Italy F23 | 2014/07/15 19:30 | Ottolini, Federico v Ehrat, Sandro | 6-2,1-6,3-6 |
| ITF Italy F23 Qual | 2014/07/13 12:25 | Capecchi, Daniele v Ottolini, Federico | 7-5,7-6 |
| ITF Italy F22 Qual | 2014/07/06 11:25 | Borella, Filippo v Ottolini, Federico | 1-6,3-6 |
| 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 | Rodriguez-Pace, Ricardo v Goncalo Oliveira | 5-7,7-5,7-6 |
| ITF Italy F14 | 2016/06/09 08:00 | Virgili, Adelchi v Goncalo Oliveira | 7-6,3-6,6-3 |
| ITF Italy F14 | 2016/06/07 12:30 | Martniez, Mateo Nicolas v Goncalo Oliveira | 6-7,2-6 |
| ITF Italy F13 | 2016/05/31 09:30 | Tatlot, Johan Sebastien v Goncalo Oliveira | 6-3,6-2 |
| ITF Italy F13 | 2016/05/30 08:00 | Goncalo Oliveira v Roberto, Riccardo | 6-1,6-3 |
| ITF Italy F13 | 2016/05/29 07:30 | Goncalo Oliveira v Bertuccioli, Federico | 6-2,6-4 |
| Challenger Vicenza Qual | 2016/05/22 12:40 | Stefano Napolitano v Goncalo Oliveira | 6-4,6-1 |