Round: 26 Ground: Hardcourt outdoor
| 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 |
| ITF Canada F5 | 2016/07/07 18:35 | Philip Bester v Alexis Galarneau | 6-4,7-5 |
| ITF Canada F5 | 2016/07/06 21:00 | Philip Bester v Victor Krustev | 6-4,6-1 |
| 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 |
| ITF USA F17 Qual | 2016/06/04 15:30 | Stefan Frljanic v Drew Van Orderlain | 4-6,6-7 |
| ITF Turkey F4 | 2016/01/23 09:30 | Stefan Frljanic v Yuta Kikuchi | 6-4,2-6,5-7 |
| ITF Turkey F3 | 2016/01/17 08:30 | Isa Mammetgulyyev v Stefan Frljanic | 6-3,6-2 |