Round: 26 Ground: Hardcourt outdoor
| ITF Canada F6 | 2016/08/30 16:00 | Bester, Philip v Scott, Harrison | 7-5,6-2 |
| Challenger Granby | 2016/08/04 22:30 | Yasutaka Uchiyama v Bester, Philip | 6-4,7-5 |
| Challenger Granby | 2016/08/02 16:05 | Bester, Philip v Quentin Halys | 6-2,7-6 |
| Challenger Winnipeg | 2016/07/15 15:00 | Bester, Philip v Gojowczyk, Peter | 5-7,3-6 |
| Challenger Winnipeg | 2016/07/14 15:20 | Fratangelo, Bjorn v Bester, Philip | 6-4,5-7,1-6 |
| Challenger Winnipeg | 2016/07/12 20:35 | Schnur, Brayden v Bester, Philip | 1-6,3-6 |
| ITF Canada F5 | 2016/07/10 17:00 | Bester, Philip v Polansky, Peter | 6-4,4-6,6-4 |
| ITF Canada F5 | 2016/07/09 17:00 | Bester, Philip v Blake Mott | 6-4,4-6,6-4 |
| ITF Canada F6 | 2016/08/30 18:05 | Stefan Frljanic v Sood, Chandril | 3-6,7-6,6-2 |
| ITF Canada F6 | 2016/08/27 16:00 | Stefan Frljanic v Hale, Darryl | 4-6,6-3,6-2 |
| ITF USA F27 Qual | 2016/08/06 14:30 | Stefan Frljanic v Landa Catan, Pablo | 6-7,2-6 |
| ITF USA F25 Qual | 2016/07/23 13:30 | Race, Warren v Stefan Frljanic | 7-5,7-6 |
| ITF Canada F4 Qual | 2016/06/27 20:15 | Furman, Spencer v Stefan Frljanic | 6-3,6-2 |
| ITF Canada F4 Qual | 2016/06/26 17:00 | Stafford, Jabari v Stefan Frljanic | 6-4,1-6,2-6 |
| ITF Canada F3 Qual | 2016/06/19 19:00 | Du Toit, Riaan v Stefan Frljanic | 7-5,6-1 |
| ITF USA F18 | 2016/06/12 13:00 | Felix Corwin v Stefan Frljanic | 7-6,6-0 |