Round: 46 Ground: Clay
| Wimbledon Qual | 2016/06/21 11:40 | Yannick Mertens v Guido Andreozzi | 6-3,6-4 |
| Challenger Perugia | 2016/06/17 11:25 | Juan Ignacio Londero v Guido Andreozzi | 6-3,6-7,6-4 |
| Challenger Perugia | 2016/06/16 15:30 | Stefano Napolitano v Guido Andreozzi | 4-6,4-6 |
| Challenger Perugia | 2016/06/14 09:00 | Frederico Ferreira Silva v Guido Andreozzi | 2-6,7-6,4-6 |
| Challenger Caltanissetta | 2016/06/11 13:00 | Guido Andreozzi v Matteo Donati | 6-4,5-7,2-6 |
| Challenger Caltanissetta | 2016/06/10 14:00 | Enrique Lopez-Perez v Guido Andreozzi | 2-6,4-6 |
| Challenger Caltanissetta | 2016/06/08 11:00 | Guido Andreozzi v Julian Reister | 3-6,6-3,6-3 |
| Challenger Caltanissetta | 2016/06/06 11:20 | Guido Andreozzi v Sumit Nagal | 6-2,6-4 |
| 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 |
| Challenger Vicenza | 2016/05/26 15:30 | Filippo Volandri v Nicolas Kicker | 2-6,1-6 |
| Challenger Vicenza | 2016/05/24 17:10 | Filippo Volandri v Marton Fucsovics | 7-6,6-2 |
| French Open Qual | 2016/05/16 09:35 | Kenny de Schepper v Filippo Volandri | 6-3,7-6 |