Round: 26 Ground: Clay
| Challenger Milan Qual | 2016/06/20 08:30 | Daniele Capecchi v Lorenzo Sonego | 4-6,2-6 |
| Challenger Milan Qual | 2016/06/19 09:30 | Daniele Capecchi v Fabrizio Ornago | 6-2,6-3 |
| Challenger Milan Qual | 2016/06/18 08:00 | Michael Linzer v Daniele Capecchi | 5-7,2-6 |
| ITF Italy F15 | 2016/06/16 17:25 | Daniele Capecchi v Joao Domingues | 2-6,1-6 |
| ITF Italy F15 | 2016/06/14 11:00 | Alberto Brizzi v Daniele Capecchi | 7-6,5-7,2-6 |
| ITF Italy F11 | 2016/05/22 08:45 | Daniele Capecchi v Gianluca Di Nicola | 7-5,3-6,2-6 |
| ITF Italy F11 | 2016/05/21 12:00 | Francisco Bahamonde v Daniele Capecchi | 3-6,5-7 |
| ITF Italy F11 | 2016/05/20 12:00 | Matteo Fago v Daniele Capecchi | 1-6,3-6 |
| Challenger Milan Qual | 2016/06/20 08:30 | Vaclav Safranek v Filippo Baldi | 6-4,7-5 |
| Challenger Milan Qual | 2016/06/19 12:00 | Filippo Baldi v Jose Hernandez-Fernandez | 7-5,6-4 |
| ITF Italy F15 | 2016/06/14 10:55 | Andrea Guerrieri v Filippo Baldi | 1-6,6-4,6-3 |
| ITF Italy F13 | 2016/06/02 09:00 | Filippo Baldi v Riccardo Bellotti | 4-6,2-6 |
| ITF Italy F13 | 2016/06/01 09:30 | Gavin Van Peperzeel v Filippo Baldi | 2-6,2-6 |
| ITF Italy F13 | 2016/05/31 08:00 | Robin Lang v Filippo Baldi | 2-6,1-6 |
| ITF Italy F12 | 2016/05/25 12:50 | Marco Bortolotti v Filippo Baldi | 3-6,7-5,7-5 |
| ITF Italy F12 | 2016/05/24 09:30 | Andrea Vavassori v Filippo Baldi | 4-6,6-7 |