Round: 25 Ground: Hardcourt indoor
| Challenger Monterrey | 2016/10/10 18:00 | Philip Bester v Adam El Mihdawy | 6-4,6-4 |
| Challenger Stockton Qual | 2016/10/03 20:10 | Dennis Nevolo v Philip Bester | 6-1,4-6,6-3 |
| Challenger Stockton Qual | 2016/10/02 17:50 | Mico Santiago v Philip Bester | 3-6,1-6 |
| Challenger Stockton Qual | 2016/10/01 20:55 | Philip Bester v Nils Langer | 6-3,7-6 |
| Challenger Columbus | 2016/09/20 16:50 | Tennys Sandgren v Philip Bester | 6-4,6-4 |
| Challenger Cary | 2016/09/15 18:45 | Philip Bester v Stefan Kozlov | 4-6,1-6 |
| Challenger Cary | 2016/09/13 16:00 | Philip Bester v Nicolas Meister | 7-5,6-3 |
| ITF Canada F7 | 2016/09/08 16:00 | David Volfson v Philip Bester | 7-6,1-6,6-3 |
| Challenger Charlottesville | 2016/11/01 15:30 | Liam Broady v JC Aragone | 6-1,3-6,6-3 |
| Challenger Charlottesville Qual | 2016/10/31 17:05 | Dominik Koepfer v JC Aragone | 3-6,6-7 |
| Challenger Charlottesville Qual | 2016/10/30 15:50 | JC Aragone v Luke Bambridge | 4-6,7-5,6-4 |
| Challenger Charlottesville Qual | 2016/10/29 14:00 | Aswin Lizen v JC Aragone | 3-6,3-6 |
| ITF USA F28 | 2015/09/30 18:40 | JC Aragone v Noah Rubin | 2-6,2-6 |
| ITF USA F25 Qual | 2015/08/10 14:00 | JC Aragone v Hunter Callahan | 5-7,3-6 |
| ITF USA F25 Qual | 2015/08/09 14:00 | Dennis Nevolo v JC Aragone | 2-6,6-3,4-6 |
| ITF USA F25 Qual | 2015/08/08 14:00 | JC Aragone v Sergey Belov | 6-2,6-4 |