Round: 29 Ground: Clay
| Challenger Szczecin | 2016/09/18 01:04 | Brown, Dustin v Alessandro Giannessi | 2-6,3-6 |
| Challenger Szczecin | 2016/09/18 01:04 | Brown, Dustin v Alessandro Giannessi | 2-6,3-6 |
| Challenger Szczecin | 2016/09/17 14:00 | Eysseric, Jonathan v Brown, Dustin | 4-6,4-6 |
| Challenger Szczecin | 2016/09/16 14:30 | Brown, Dustin v Salvatore Caruso | 4-6,6-3,6-3 |
| Challenger Szczecin | 2016/09/14 12:00 | Brown, Dustin v Mathias Bourgue | 6-1,6-1 |
| Challenger Szczecin | 2016/09/13 12:15 | Brown, Dustin v Ivanov, Vladimir | 6-3,6-7,6-2 |
| US Open, New York, USA | 2016/08/29 23:00 | Brown, Dustin v Milos Raonic | 5-7,3-6,4-6 |
| ATP Bastad | 2016/07/15 13:10 | FERRER D. v Brown, Dustin | 6-1,4-6,6-4 |
| ATP Bastad | 2016/07/14 09:00 | Brown, Dustin v Bedene, Aljaz | 6-3,6-7,6-3 |
| Challenger Szczecin | 2016/09/18 01:04 | Brown, Dustin 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 |
| 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, New York, USA, Qualifying | 2016/08/26 20:20 | Alessandro Giannessi v Kamke, Tobias | 7-5,6-1 |