Round: 44 Ground: Clay
| ITF Italy F24 Qual | 2016/08/07 12:05 | Sebastian Prechtel v Andres Gabriel Ciurletti | 6-4,5-7,6-2 |
| ITF Italy F24 Qual | 2016/08/06 08:30 | Manuel Bernard v Andres Gabriel Ciurletti | 0-6,1-6 |
| ITF Italy F23 | 2016/08/02 08:30 | Andres Gabriel Ciurletti v Francesco Ferrari | 5-7,6-1,3-6 |
| ITF Italy F23 Qual | 2016/08/01 08:40 | Andres Gabriel Ciurletti v Stefano Reitano | 6-3,6-0 |
| ITF Italy F23 Qual | 2016/07/30 07:30 | Andres Gabriel Ciurletti v Giovanni Narcisi | 6-4,5-7,6-3 |
| ITF Italy F22 | 2016/07/27 16:30 | Andres Gabriel Ciurletti v Marco Bortolotti | 3-6,2-6 |
| ITF Italy F22 | 2016/07/25 10:55 | Andres Gabriel Ciurletti v Oliver Mrose | 7-6,6-2 |
| ITF Italy F21 | 2016/07/18 11:00 | Andres Gabriel Ciurletti v Tommaso Gabrieli | 5-7,4-6 |
| ITF Italy F25 Qual | 2016/08/13 08:00 | Riccardo Roberto v Alessandro Ragazzi | 6-0,6-3 |
| ITF Italy F14 Qual | 2016/06/05 11:50 | Toby Martin v Riccardo Roberto | 6-3,6-3 |
| ITF Italy F14 Qual | 2016/06/04 10:45 | Riccardo Roberto v Facundo Jofre | 7-5,6-2 |
| ITF Italy F13 | 2016/05/30 08:00 | Goncalo Oliveira v Riccardo Roberto | 6-1,6-3 |
| ITF Italy F13 | 2016/05/29 07:30 | Cristiano Russo v Riccardo Roberto | 5-7,6-4,2-6 |
| ITF Italy F13 | 2016/05/28 08:30 | Riccardo Roberto v Gil Uwe Grund | 6-2,7-6 |
| ITF Italy F11 Qual | 2016/05/16 14:55 | Cristian Carli v Riccardo Roberto | 6-2,6-3 |
| ITF Italy F11 Qual | 2016/05/16 10:10 | Riccardo Roberto v Augusto Virgili | 7-6,6-3 |