Stadium: CENTER Round: 25 Ground: Hardcourt outdoor
| Challenger Tiburon Qual | 2016/09/26 17:00 | Matt Reid v Brydan Klein | 3-6,5-7 |
| Challenger Tiburon Qual | 2016/09/25 19:25 | Connor Farren v Brydan Klein | 1-6,1-6 |
| Challenger Tiburon Qual | 2016/09/24 17:00 | Andrew Carter v Brydan Klein | 6-4,2-6,1-6 |
| Challenger Columbus | 2016/09/20 15:00 | Roberto Quiroz v Brydan Klein | 6-4,6-2 |
| Challenger Cary | 2016/09/14 17:00 | Dennis Novikov v Brydan Klein | 6-4,6-4 |
| Challenger Cary | 2016/09/12 17:30 | Brydan Klein v Sekou Bangoura | 1-6,7-5,6-2 |
| Challenger Granby | 2016/08/02 19:45 | Brydan Klein v Gregoire Barrere | 3-6,3-6 |
| ATP Newport Qual | 2016/07/11 16:25 | Brydan Klein v Brian Baker | 6-7,4-6 |
| US Open Qual | 2016/08/25 17:00 | Tim Smyczek v Guilherme Clezar | 6-7,3-6 |
| US Open Qual | 2016/08/23 18:55 | Tim Smyczek v Alexander Kudryavtsev | 6-3,6-4 |
| ATP Cincinnati Qual | 2016/08/13 19:25 | Jiri Vesely v Tim Smyczek | 6-4,6-2 |
| ATP Washington | 2016/07/18 20:00 | James Duckworth v Tim Smyczek | 7-5,6-1 |
| Challenger Winnipeg | 2016/07/14 15:35 | Tim Smyczek v Daniel Nguyen | 2-6,3-6 |
| Challenger Winnipeg | 2016/07/11 15:00 | Tim Smyczek v Kevin Kylar | 6-1,6-1 |
| Wimbledon Qual | 2016/06/22 12:15 | Tim Smyczek v Hiroki Moriya | 1-6,6-3,4-6 |
| Wimbledon Qual | 2016/06/20 18:05 | Tim Smyczek v Ilya Ivashka | 7-6,6-2 |