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 | Salisbury, Joe 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 | Lorenzi, Paolo v Alessandro Giannessi | 6-4,7-5 |
| Challenger Caltanissetta | 2016/06/10 13:00 | Alessandro Giannessi v Arevalo-Gonzalez, Marcelo | 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 Harrison, Ryan | 3-6,2-6 |
| Challenger Todi | 2016/07/06 09:00 | Gregoire Barrere v de Greef, Arthur | 3-6,7-5,4-6 |
| Challenger Marburg | 2016/06/28 14:00 | de Greef, Arthur v Dimitar Kuzmanov | 3-6,6-7 |
| Challenger Milan Qual | 2016/06/24 14:10 | de Greef, Arthur v Marco Cecchinato | 3-6,2-6 |
| Challenger Milan Qual | 2016/06/23 10:00 | Dutra Silva, Rogerio v de Greef, Arthur | 7-6,2-6,3-6 |
| Challenger Milan Qual | 2016/06/21 09:50 | Nicolas Jarry v de Greef, Arthur | 5-7,3-6 |
| French Open Qual | 2016/05/18 11:45 | de Greef, Arthur v Berlocq, Carlos | 3-6,7-5,7-9 |
| French Open Qual | 2016/05/16 14:35 | Zopp, Jurgen v de Greef, Arthur | 5-7,6-7 |
| Challenger Heilbronn Qual | 2016/05/07 08:00 | de Greef, Arthur v Tom Schonenberg | 6-4,7-5 |