Round: 26 Ground: Hardcourt outdoor
| ITF Canada F1 | 2015/03/04 22:00 | Philip Bester v David Volfson | 6-2,7-5 |
| ITF Canada F7 | 2016/09/05 20:00 | David Volfson v Alex Rybakov | 6-7,6-2,6-2 |
| ITF Finland F3 | 2016/08/15 22:00 | David Volfson v Robbie Mudge | 6-4,4-6,4-6 |
| ITF Finland F3 Qual | 2016/08/14 22:00 | David Volfson v Jonathan Stenberg | 6-4,3-6,6-3 |
| ITF Finland F3 Qual | 2016/08/12 22:00 | David Volfson v Peter Sillanpaa | 6-1,6-1 |
| ITF Latvia F1 | 2016/08/03 07:00 | Claudio Fortuna v David Volfson | 6-3,6-3 |
| ITF Latvia F1 | 2016/08/02 07:00 | Harrison Lombe v David Volfson | 0-6,0-6 |
| ITF Georgia F1 | 2016/07/28 10:40 | Baptiste Crepatte v David Volfson | 6-3,6-2 |
| ITF Lithuania F1 | 2016/07/19 10:15 | David Volfson v Pirmin Haenle | 6-7,2-6 |
| 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 Winnipeg | 2016/07/15 15:00 | Philip Bester v Peter Gojowczyk | 5-7,3-6 |