Round: 27 Ground: Hardcourt outdoor
| Challenger Tiburon | 2016/09/27 17:00 | Yuki Bhambri v Darian King | 2-6,6-3,3-6 |
| Challenger Cary | 2016/09/15 17:00 | James McGee v Darian King | 6-1,6-3 |
| Challenger Cary | 2016/09/13 16:00 | Nicolaas Scholtz v Darian King | 4-6,4-6 |
| Challenger Barranquilla | 2016/09/06 15:30 | Roberto Quiroz v Darian King | 0-6,6-3,6-2 |
| US Open Qual | 2016/08/25 19:00 | Aleksandr Nedovyesov v Darian King | 6-3,5-7,6-3 |
| US Open Qual | 2016/08/23 20:25 | Darian King v Grega Zemlja | 4-6,6-4,6-4 |
| Challenger Cali 2 | 2016/07/10 16:00 | Victor Estrella Burgos v Darian King | 7-5,4-6,5-7 |
| Challenger Cali 2 | 2016/07/09 17:35 | Jose Hernandez-Fernandez v Darian King | 6-7,3-6 |
| Challenger Tiburon | 2016/09/29 18:00 | Brian Baker v Dennis Novikov | 4-6,6-3,1-6 |
| Challenger Tiburon | 2016/09/27 23:55 | Robbie C Bellamy v Dennis Novikov | 3-6,2-6 |
| Challenger Columbus | 2016/09/20 14:00 | Evan King v Dennis Novikov | 6-4,6-7,7-6 |
| Challenger Cary | 2016/09/17 18:10 | Dennis Novikov v James McGee | 6-3,3-6,3-6 |
| Challenger Cary | 2016/09/16 16:00 | Dennis Novikov v Peter Polansky | 6-3,2-6,6-4 |
| Challenger Cary | 2016/09/14 17:00 | Dennis Novikov v Brydan Klein | 6-4,6-4 |
| Challenger Cary | 2016/09/12 17:30 | Dennis Novikov v Mikelis Libietis | 7-6,6-4 |
| US Open Qual | 2016/08/25 19:30 | Dennis Novikov v Pedja Krstin | 6-7,5-7 |