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