Stadium: STADIUM Round: 25
| Challenger Tiburon Qual | 2016/09/25 20:20 | Alessandro Giannessi v Matt Reid | 6-7,5-7 |
| Challenger Szczecin | 2016/09/18 10:00 | Dustin Brown v Alessandro Giannessi | 2-6,3-6 |
| Challenger Szczecin | 2016/09/18 01:04 | Dustin Brown v Alessandro Giannessi | 2-6,3-6 |
| Challenger Szczecin | 2016/09/17 12:00 | Alessandro Giannessi v Constant Lestienne | 6-3,6-3 |
| Challenger Szczecin | 2016/09/16 14:15 | Stefano Napolitano v Alessandro Giannessi | 3-6,6-7 |
| Challenger Szczecin | 2016/09/15 13:00 | Akira Santillan v Alessandro Giannessi | 3-6,3-6 |
| Challenger Szczecin | 2016/09/13 16:05 | Alessandro Giannessi v Radu Albot | 6-3,6-4 |
| US Open 2016 | 2016/09/01 23:55 | Alessandro Giannessi v Stan Wawrinka | 1-6,6-7,5-7 |