Round: 26 Ground: Hardcourt outdoor
| 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 F5 | 2016/07/09 17:00 | Philip Bester v Blake Mott | 6-4,4-6,6-4 |
| ITF Canada F6 | 2016/08/30 18:05 | Stefan Frljanic v Chandril Sood | 3-6,7-6,6-2 |
| ITF Canada F6 | 2016/08/27 16:00 | Stefan Frljanic v Darryl Hale | 4-6,6-3,6-2 |
| ITF USA F27 Qual | 2016/08/06 14:30 | Stefan Frljanic v Pablo Landa Catan | 6-7,2-6 |
| ITF USA F25 Qual | 2016/07/23 13:30 | Warren Race v Stefan Frljanic | 7-5,7-6 |
| ITF Canada F4 Qual | 2016/06/27 20:15 | Spencer Furman v Stefan Frljanic | 6-3,6-2 |
| ITF Canada F4 Qual | 2016/06/26 17:00 | Jabari Stafford v Stefan Frljanic | 6-4,1-6,2-6 |
| ITF Canada F3 Qual | 2016/06/19 19:00 | Riaan Du Toit v Stefan Frljanic | 7-5,6-1 |
| ITF USA F18 | 2016/06/12 13:00 | Felix Corwin v Stefan Frljanic | 7-6,6-0 |