Round: 25 Ground: Hardcourt outdoor
| ITF Canada F3 | 2016/06/22 18:35 | Kevin Kylar v Philip Bester | 2-6,1-6 |
| ITF Canada F3 | 2016/06/24 18:00 | Peter Polansky v Philip Bester | 4-6,6-3,6-2 |
| ITF Canada F3 | 2016/06/23 17:00 | Michael Genender v Philip Bester | 1-6,0-6 |
| ITF Canada F3 | 2016/06/22 18:35 | Kevin Kylar v Philip Bester | 2-6,1-6 |
| ITF USA F17 | 2016/06/08 15:50 | Philip Bester v Dominic Cotrone | 6-3,3-6,6-3 |
| ITF USA F16 | 2016/05/07 14:00 | Roberto Quiroz v Philip Bester | 6-2,6-4 |
| ITF USA F16 | 2016/05/06 14:00 | Philip Bester v Miomir Kecmanovic | 7-5,6-3 |
| ITF USA F16 | 2016/05/05 18:00 | Philip Bester v Matias Franco Descotte | 7-6,6-3 |
| ITF USA F16 | 2016/05/05 14:50 | Philip Bester v Victor Krustev | 6-3,6-2 |
| ITF Canada F3 | 2016/06/22 18:35 | Kevin Kylar v Philip Bester | 2-6,1-6 |
| ITF Bulgaria F1 | 2016/05/18 09:30 | Aliaksandr Prudnikau v Kevin Kylar | 6-3,6-1 |
| ITF USA F12 Qual | 2016/04/04 14:00 | Denis Shapovalov v Kevin Kylar | 6-2,6-0 |
| ITF USA F10 Qual | 2016/03/12 21:00 | Evan Zhu v Kevin Kylar | 6-1,4-6,6-3 |
| ITF Canada F1 Qual | 2016/02/29 15:00 | Kevin Kylar v Jack Mingjie Lin | 4-6,1-6 |
| ITF Canada F1 Qual | 2016/02/28 15:00 | Kevin Kylar v Ivan Mitric | 6-3,6-1 |
| ITF Israel F11 | 2015/09/02 10:10 | Bar Tzuf Botzer v Kevin Kylar | 6-1,6-2 |
| ITF Canada F6 | 2015/07/30 17:00 | Kevin Kylar v Matt Reid | 0-6,4-6 |