Round: 25 Ground: Clay
| 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 Buenos Aires 2 Qual | 2016/10/09 15:10 | Daniel Dutra Da Silva v Axel Geller | 6-1,6-1 |
| Challenger Buenos Aires 2 Qual | 2016/10/08 15:10 | Axel Geller v Alejo Vilaro | 7-5,6-7,6-3 |
| ITF Argentina F9 | 2016/05/30 22:00 | Oscar Jose Gutierrez v Axel Geller | 7-6,6-2 |