Round: 27 Ground: Hardcourt outdoor
| 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 Winnipeg | 2016/07/15 15:00 | Philip Bester v Peter Gojowczyk | 5-7,3-6 |
| Challenger Winnipeg | 2016/07/14 15:20 | Bjorn Fratangelo v Philip Bester | 6-4,5-7,1-6 |
| Challenger Winnipeg | 2016/07/12 20:35 | Brayden Schnur v Philip Bester | 1-6,3-6 |
| ITF Canada F5 | 2016/07/10 17:00 | Philip Bester v Peter Polansky | 6-4,4-6,6-4 |
| ITF Canada F6 | 2016/09/01 18:20 | Serge Becerra v Gonzales Austin | 0-6,3-6 |
| ITF USA F27 | 2016/08/10 17:30 | Gonzales Austin v Wil Spencer | 3-6,6-7 |
| ITF USA F27 | 2016/08/08 16:50 | Alejandro Gomez v Gonzales Austin | 6-7,3-6 |
| ITF USA F26 | 2016/08/04 19:45 | Evan King v Gonzales Austin | 6-2,5-7,6-4 |
| ITF USA F26 | 2016/08/02 15:00 | Aron Hiltzik v Gonzales Austin | 5-7,6-7 |
| ITF USA F25 | 2016/07/26 14:00 | Gonzales Austin v Rhyne Williams | 1-6,2-6 |
| ITF USA F24 | 2016/07/20 16:30 | Rhyne Williams v Gonzales Austin | 6-2,6-2 |
| ITF Canada F4 | 2016/06/29 17:00 | Gonzales Austin v Filip Peliwo | 6-4,3-6,4-6 |