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