Round: 26 Ground: Hardcourt outdoor
| Challenger Knoxville | 2016/11/10 15:00 | Tim Smyczek v Michael Mmoh | 3-6,2-6 |
| Challenger Knoxville | 2016/11/09 16:20 | Tim Smyczek v Tim Van Rijthoven | 7-6,6-4 |
| Challenger Charlottesville | 2016/11/04 23:05 | Tim Smyczek v Ruben Bemelmans | 2-6,4-6 |
| Challenger Charlottesville | 2016/11/03 16:00 | Tim Smyczek v Brian Baker | 7-5,6-4 |
| Challenger Charlottesville | 2016/11/01 20:50 | Tim Smyczek v Thai-Son Kwiatkowski | 6-4,2-6,6-3 |
| Challenger Fairfield | 2016/10/12 21:20 | Joris De Loore v Tim Smyczek | 6-4,7-6 |
| Challenger Fairfield | 2016/10/10 19:00 | Denis Shapovalov v Tim Smyczek | 2-6,4-6 |
| Challenger Stockton | 2016/10/05 17:00 | Mackenzie McDonald v Tim Smyczek | 6-4,6-4 |
| Challenger Knoxville | 2016/11/13 18:00 | Peter Polansky v Michael Mmoh | 5-7,6-2,1-6 |
| Challenger Knoxville | 2016/11/12 15:00 | Peter Polansky v Jared Donaldson | 6-2,6-4 |
| Challenger Knoxville | 2016/11/10 16:45 | Daniel Evans v Peter Polansky | 6-1,6-7,2-6 |
| Challenger Knoxville | 2016/11/09 15:00 | Peter Polansky v Liam Broady | 6-3,6-4 |
| Challenger Charlottesville | 2016/11/04 19:25 | Mackenzie McDonald v Peter Polansky | 7-5,6-4 |
| Challenger Charlottesville | 2016/11/03 20:05 | Austin Krajicek v Peter Polansky | 2-6,4-6 |
| Challenger Charlottesville | 2016/11/01 18:05 | Noah Rubin v Peter Polansky | 3-6,2-6 |
| Challenger Las Vegas | 2016/10/18 18:40 | Tucker Vorster v Peter Polansky | 4-6,6-7 |