Round: 26 Ground: Clay
| French Open Qual | 2016/05/19 10:45 | Federico Gaio v Guido Andreozzi | 6-7,5-7 |
| 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 |
| Wimbledon Qual | 2016/06/20 17:25 | Alexandre Sidorenko v Federico Gaio | 7-6,3-6,6-3 |
| Challenger Vicenza Qual | 2016/05/23 08:00 | Federico Gaio v Stefano Napolitano | 4-6,4-6 |
| Challenger Vicenza Qual | 2016/05/22 14:15 | Federico Gaio v Danilo Petrovic | 7-6,6-7,6-4 |
| Challenger Vicenza Qual | 2016/05/21 14:45 | Federico Gaio v Matteo Viola | 6-4,5-7,6-2 |
| French Open Qual | 2016/05/19 10:45 | Federico Gaio v Guido Andreozzi | 6-7,5-7 |
| French Open Qual | 2016/05/17 09:25 | Uladzimir Ignatik v Federico Gaio | 6-7,7-6,7-9 |
| Challenger St Brieuc | 2016/04/01 10:20 | Aleksandr Nedovyesov v Federico Gaio | 6-3,6-1 |
| Challenger St Brieuc | 2016/03/31 10:30 | Federico Gaio v Remi Boutillier | 6-4,3-6,7-6 |