Round: 25 Ground: Hardcourt outdoor
| 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 F5 | 2016/07/08 19:10 | Philip Bester v Brayden Schnur | 6-3,6-2 |
| Challenger Aptos Qual | 2016/08/06 17:30 | Cameron Norrie v Harrison Scott | 6-0,6-4 |
| ITF Germany F9 | 2016/08/01 08:00 | Harrison Scott v Mark-Flavius Andres | 3-6,3-6 |
| ITF Canada F3 | 2016/06/21 20:00 | Riaan Du Toit v Harrison Scott | 1-6,6-2,0-6 |
| ITF USA F34 Qual | 2015/11/23 16:00 | Harrison Scott v Jakob Sude | 4-6,0-6 |
| ITF Canada F8 | 2015/09/03 17:45 | Harrison Scott v Frank Dancevic | 1-6,2-6 |
| ITF Canada F8 | 2015/09/02 18:25 | Harrison Scott v Luis David Martinez | 6-3,4-6,7-5 |
| ITF Canada F6 | 2015/07/29 01:00 | Denis Shapovalov v Harrison Scott | 6-0,7-6 |
| ITF Canada F5 | 2015/07/23 19:25 | Finn Tearney v Harrison Scott | 6-0,6-2 |