Ground: Clay
| Challenger Szczecin | 2016/09/17 14:00 | Jonathan Eysseric v Dustin Brown | 4-6,4-6 |
| Challenger Szczecin | 2016/09/16 14:30 | Dustin Brown v Salvatore Caruso | 4-6,6-3,6-3 |
| Challenger Szczecin | 2016/09/14 12:00 | Dustin Brown v Mathias Bourgue | 6-1,6-1 |
| Challenger Szczecin | 2016/09/13 12:15 | Dustin Brown v Vladimir Ivanov | 6-3,6-7,6-2 |
| US Open | 2016/08/29 23:00 | Dustin Brown v Milos Raonic | 5-7,3-6,4-6 |
| ATP Båstad | 2016/07/15 13:10 | David Ferrer v Dustin Brown | 6-1,4-6,6-4 |
| ATP Båstad | 2016/07/14 09:00 | Dustin Brown v Aljaz Bedene | 6-3,6-7,6-3 |
| ATP Båstad | 2016/07/12 11:15 | Dustin Brown v Daniel Munoz-De La Nava | 6-2,7-6 |
| 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 |
| US Open 2016 | 2016/08/30 17:20 | Denis Kudla v Alessandro Giannessi | 6-0,4-6,1-6,6-1,0-6 |
| US Open Qual | 2016/08/26 20:20 | Alessandro Giannessi v Tobias Kamke | 7-5,6-1 |
| US Open Qual | 2016/08/25 23:45 | Yuichi Sugita v Alessandro Giannessi | 3-6,6-3,5-7 |