Stadium: COURT 1 Round: 26 Ground: Hardcourt outdoor
| Challenger Stockton | 2016/10/04 20:10 | Sekou Bangoura v Darian King | 0-6,3-6 |
| Challenger Tiburon | 2016/10/02 21:25 | Darian King v Michael Mmoh | 7-6,6-2 |
| Challenger Tiburon | 2016/10/01 19:50 | Darian King v Mackenzie McDonald | 4-6,7-5,7-5 |
| Challenger Tiburon | 2016/09/30 19:00 | Darian King v Dennis Novikov | 7-5,6-2 |
| 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 |
| Challenger Columbus | 2016/09/24 18:30 | Mikael Torpegaard v Tennys Sandgren | 7-5,7-6 |
| Challenger Columbus | 2016/09/23 16:00 | Tennys Sandgren v Roberto Quiroz | 6-0,7-6 |
| Challenger Columbus | 2016/09/21 17:10 | Blaz Rola v Tennys Sandgren | 6-7,3-6 |
| Challenger Columbus | 2016/09/20 16:50 | Tennys Sandgren v Philip Bester | 6-4,6-4 |
| Challenger Cary | 2016/09/17 00:10 | Tennys Sandgren v Frances Tiafoe | 4-6,6-1,6-7 |
| Challenger Cary | 2016/09/14 17:00 | Cameron Norrie v Tennys Sandgren | 6-7,3-6 |
| Challenger Cary | 2016/09/13 16:00 | Tennys Sandgren v Mackenzie McDonald | 6-4,6-3 |
| US Open Qual | 2016/08/23 20:10 | Jurgen Melzer v Tennys Sandgren | 7-5,6-1 |