Round: 25 Ground: Hardcourt outdoor
| 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 |
| ITF Canada F6 | 2016/08/30 16:00 | Philip Bester v Harrison Scott | 7-5,6-2 |
| Challenger Granby | 2016/08/04 22:30 | Yasutaka Uchiyama v Philip Bester | 6-4,7-5 |
| Challenger Granby | 2016/08/02 16:05 | Philip Bester v Quentin Halys | 6-2,7-6 |
| Challenger Aptos | 2016/08/08 20:30 | Nicolas Meister v James McGee | 6-4,5-7,5-7 |
| Challenger Winnipeg | 2016/07/12 19:35 | Nicolas Meister v James McGee | 2-6,2-6 |
| ITF USA F23 | 2016/06/30 14:00 | Ryan Haviland v Nicolas Meister | 6-4,7-6 |
| ITF USA F23 | 2016/06/29 14:00 | Matic Spec v Nicolas Meister | 7-6,3-6,1-6 |
| ITF Israel F8 | 2016/05/28 07:00 | Nicolas Meister v Bar Tzuf Botzer | 6-3,6-4 |
| ITF Israel F8 | 2016/05/27 07:00 | Nicolas Meister v Daniel Cukierman | 4-6,6-4,6-3 |
| ITF Israel F8 | 2016/05/26 06:30 | Nicolas Meister v Ben Patael | 1-6,6-2,6-2 |
| ITF Israel F8 | 2016/05/25 06:30 | Nicolas Meister v Daniel Dudockin | 6-3,6-4 |