Round: 25 Ground: Hardcourt outdoor
| 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 Canada F6 | 2016/09/03 18:00 | Philip Bester v Brayden Schnur | 4-6,6-3,3-6 |
| ITF Canada F6 | 2016/09/02 18:15 | Philip Bester v Gonzales Austin | 7-5,6-3 |
| ITF Canada F6 | 2016/09/01 18:55 | Philip Bester v Stefan Frljanic | 4-6,7-6,7-5 |
| Challenger Kenitra | 2016/09/20 09:30 | Federico Coria v Nils Langer | 6-1,6-4 |
| Challenger Meknes | 2016/09/14 10:00 | Yannik Reuter v Nils Langer | 4-6,4-6 |
| Challenger Meknes | 2016/09/14 09:50 | Yannick Reuter v Nils Langer | 4-6,4-6 |
| Challenger Meknes | 2016/09/13 09:00 | Alexander Zhurbin v Nils Langer | 4-6,3-6 |
| Challenger - Como | 2016/09/02 09:00 | Taro Daniel v Nils Langer | 6-1,6-4 |
| Challenger - Como | 2016/08/31 09:00 | Nils Langer v Albert Montanes | 7-6,6-4 |
| Challenger - Como | 2016/08/29 08:00 | Gianluca Mager v Nils Langer | 3-6,1-6 |
| Challenger Manerbio | 2016/08/26 15:30 | Matteo Donati v Nils Langer | 6-7,6-4,6-3 |