Round: 25 Ground: Hardcourt outdoor
| Challenger Le Gosier | 2016/04/05 19:00 | Philip Bester v Andre Ghem | 4-6,6-7 |
| Challenger Drummondville | 2016/03/18 17:00 | Philip Bester v Daniel Evans | 3-6,6-7 |
| Challenger Drummondville | 2016/03/17 18:30 | Philip Bester v Roberto Ortega-Olmedo | 6-3,7-6 |
| Challenger Drummondville | 2016/03/15 22:30 | Tommy Paul v Philip Bester | 3-6,4-6 |
| Davis Cup | 2016/03/06 15:15 | Richard Gasquet v Philip Bester | 6-1,7-6 |
| Challenger Morelos | 2016/02/17 16:00 | Alejandro Gonzalez v Philip Bester | 7-5,7-6 |
| Challenger Morelos | 2016/02/15 18:05 | Tigre Hank v Philip Bester | 3-6,6-7 |
| ITF USA F2 | 2016/01/13 20:50 | Yannick Hanfmann v Philip Bester | 6-4,4-6,6-3 |
| 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 |
| ITF USA F21 | 2015/06/30 15:15 | Jared Hiltzik v Kevin Kylar | 6-4,6-1 |
| ITF Georgia F2 | 2015/06/10 08:00 | Kevin Kylar v Marek Rehacek | 3-6,2-6 |