Stadium: CANCHA 1 Round: 25 Ground: Hardcourt outdoor
| 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 |
| ITF Canada F7 | 2016/09/06 17:35 | Andrew Carter v Philip Bester | 3-6,2-6 |
| ITF Colombia F4 | 2016/10/04 17:00 | Adam El Mihdawy v Gregorio Cordonnier | 6-2,6-3 |
| Challenger Medellin | 2016/09/28 20:05 | Joao Souza v Adam El Mihdawy | 6-2,6-3 |
| Challenger Medellin | 2016/09/27 19:45 | Daniel Elahi Galan v Adam El Mihdawy | 4-6,3-6 |
| ITF Canada F9 Qual | 2016/09/25 15:00 | Adam El Mihdawy v Brayden Schnur | 4-6,7-5,6-4 |
| ITF Canada F9 Qual | 2016/09/24 15:00 | Adam El Mihdawy v Alejandro Tabilo | 6-4,6-3 |
| ITF Canada F9 Qual | 2016/09/23 19:50 | Adam El Mihdawy v Pavel Krainik | 6-4,6-2 |
| ITF Canada F9 Qual | 2016/09/22 17:15 | Adam El Mihdawy v Raleigh Smith | 3-6,6-4,6-2 |
| ITF Canada F9 Qual | 2016/09/21 14:00 | Adam El Mihdawy v Andrew Carter | 6-1,6-1 |