Stadium: EVE ZIMMERMAN COURT Round: 25 Ground: Hardcourt outdoor
| Challenger Stockton | 2016/10/07 17:00 | Alessandro Giannessi v Frances Tiafoe | 6-7,3-6 |
| Challenger Stockton | 2016/10/05 18:15 | Alessandro Giannessi v Daniel Nguyen | 4-6,7-5,7-5 |
| Challenger Stockton | 2016/10/04 22:50 | Alessandro Giannessi v Jose Chamba Gomez | 6-1,6-4 |
| 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 Stockton Qual | 2016/10/01 21:00 | James McGee v Eric Quigley | 2-6,1-6 |
| Challenger Cary | 2016/09/18 18:20 | James McGee v Ernesto Escobedo | 1-6,6-1,6-4 |
| Challenger Cary | 2016/09/17 18:10 | Dennis Novikov v James McGee | 6-3,3-6,3-6 |
| Challenger Cary | 2016/09/16 17:45 | Brayden Schnur v James McGee | 2-6,4-6 |
| Challenger Cary | 2016/09/15 17:00 | James McGee v Darian King | 6-1,6-3 |
| Challenger Cary | 2016/09/13 19:40 | James McGee v Evan King | 7-5,7-6 |
| Challenger Cary Qual | 2016/09/12 18:25 | James McGee v Robert Kelly | 6-1,6-1 |
| Challenger Cary Qual | 2016/09/11 18:15 | James McGee v Dominik Koepfer | 4-6,6-3,6-2 |