Round: 26 Ground: Clay
| Challenger Todi | 2016/07/05 09:00 | Alessandro Giannessi v Steven Diez | 5-7,7-5,6-1 |
| Wimbledon Qual | 2016/06/21 11:20 | Joe Salisbury v Alessandro Giannessi | 4-6,7-6,6-3 |
| Challenger Perugia | 2016/06/15 09:00 | Nicolas Kicker v Alessandro Giannessi | 6-2,6-0 |
| Challenger Caltanissetta | 2016/06/11 15:30 | Paolo Lorenzi v Alessandro Giannessi | 6-4,7-5 |
| Challenger Caltanissetta | 2016/06/10 13:00 | Alessandro Giannessi v Marcelo Arevalo | 6-4,6-1 |
| Challenger Caltanissetta | 2016/06/09 11:00 | Elias Ymer v Alessandro Giannessi | 4-6,4-6 |
| Challenger Caltanissetta | 2016/06/07 09:30 | Nicolas Jarry v Alessandro Giannessi | 6-4,5-7,4-6 |
| French Open Qual | 2016/05/16 14:30 | Alessandro Giannessi v Ryan Harrison | 3-6,2-6 |
| Challenger Todi | 2016/07/06 09:00 | Gregoire Barrere v Arthur De Greef | 3-6,7-5,4-6 |
| Challenger Marburg | 2016/06/28 14:00 | Arthur De Greef v Dimitar Kuzmanov | 3-6,6-7 |
| Challenger Milan Qual | 2016/06/24 14:10 | Arthur De Greef v Marco Cecchinato | 3-6,2-6 |
| Challenger Milan Qual | 2016/06/23 10:00 | Rogerio Dutra Silva v Arthur De Greef | 7-6,2-6,3-6 |
| Challenger Milan Qual | 2016/06/21 09:50 | Nicolas Jarry v Arthur De Greef | 5-7,3-6 |
| French Open Qual | 2016/05/18 11:45 | Arthur De Greef v Carlos Berlocq | 3-6,7-5,7-9 |
| French Open Qual | 2016/05/16 14:35 | Jurgen Zopp v Arthur De Greef | 5-7,6-7 |
| Challenger Heilbronn Qual | 2016/05/07 08:00 | Arthur De Greef v Tom Schonenberg | 6-4,7-5 |