Round: 25 Ground: Clay
| Genoa, Italy | 2015/09/10 13:00 | Lorenzi, Paolo v Volandri, Filippo | 2-6,5-7 |
| Kitzbuhel, Austria | 2016/07/23 11:00 | Lorenzi, Paolo v Nikoloz Basilashvili | 6-3,6-4 |
| Kitzbuhel, Austria | 2016/07/22 12:25 | Gerald Melzer v Lorenzi, Paolo | 6-7,6-7 |
| Kitzbuhel, Austria | 2016/07/21 12:00 | Lorenzi, Paolo v Jan-Lennard Struff | 6-2,6-7,7-5 |
| Kitzbuhel, Austria | 2016/07/20 09:00 | Lorenzi, Paolo v Roberto Carballes Baena | 6-2,6-2 |
| Wimbledon, London, Great Britain | 2016/06/27 10:30 | Lorenzi, Paolo v Lacko, Lukas | 4-6,7-6,5-7,3-6 |
| ATP Halle | 2016/06/15 10:00 | Lorenzi, Paolo v Gabashvili, Teimuraz | 1-6,4-6 |
| Challenger Caltanissetta | 2016/06/12 16:05 | Lorenzi, Paolo v Donati, Matteo | 6-3,4-6,7-6 |
| Challenger Caltanissetta | 2016/06/11 15:30 | Lorenzi, Paolo v Alessandro Giannessi | 6-4,7-5 |
| Kitzbuhel, Austria | 2016/07/18 10:30 | Karen Khachanov v Volandri, Filippo | 6-2,6-4 |
| Kitzbühel, Autriche, Qualifications | 2016/07/17 10:30 | Guido Andreozzi v Volandri, Filippo | 6-0,2-6,3-6 |
| Kitzbühel, Autriche, Qualifications | 2016/07/16 09:00 | Langer, Nils v Volandri, Filippo | 1-6,6-2,6-7 |
| Challenger Milan Qual | 2016/06/23 16:35 | Gimeno-Traver, Daniel v Volandri, Filippo | 6-2,2-6,6-0 |
| Challenger Milan Qual | 2016/06/21 15:35 | Volandri, Filippo v Lorenzo Sonego | 6-3,6-3 |
| Challenger Perugia | 2016/06/15 12:05 | Dutra Silva, Rogerio v Volandri, Filippo | 6-2,7-6 |
| Challenger Perugia | 2016/06/13 15:35 | Volandri, Filippo v Arnaboldi, Andrea | 6-4,6-7,6-4 |
| Challenger Caltanissetta | 2016/06/07 16:35 | Laslo Djere v Volandri, Filippo | 7-6,6-7,6-2 |