Stadium: Court 7 Round: 27 Ground: Hardcourt indoor
| 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 Stockton | 2016/10/04 19:35 | Grega Zemlja v Tim Smyczek | 4-6,6-3,1-6 |
| Challenger Tiburon | 2016/10/01 22:45 | Tim Smyczek v Michael Mmoh | 6-2,3-6,6-7 |
| Challenger Tiburon | 2016/09/30 19:20 | Mitchell Krueger v Tim Smyczek | 2-6,4-6 |
| Challenger Charlottesville | 2016/11/03 17:50 | Ruben Bemelmans v Bjorn Fratangelo | 6-7,6-4,6-2 |
| Challenger Charlottesville | 2016/11/02 16:00 | Sam Barry v Ruben Bemelmans | 1-6,2-6 |
| ITF USA F34 | 2016/10/30 19:00 | Ruben Bemelmans v Sam Barry | 6-1,6-2 |
| ITF USA F34 | 2016/10/29 19:00 | Ruben Bemelmans v Raymond Sarmiento | 6-2,6-3 |
| ITF USA F34 | 2016/10/28 20:35 | Ruben Bemelmans v Sebastian Fanselow | 2-6,7-6,6-1 |
| ITF USA F34 | 2016/10/27 17:00 | Ruben Bemelmans v Connor Farren | 6-0,6-2 |
| ITF USA F34 | 2016/10/25 17:00 | Ruben Bemelmans v Andrew Carter | 6-1,6-3 |
| ITF USA F33 | 2016/10/22 18:25 | Ruben Bemelmans v Marcos Giron | 6-1,3-6,5-7 |