Round: 26 Ground: Hardcourt indoor
| 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 F1 | 2016/01/10 19:00 | Stefan Kozlov v Philip Bester | 7-6,6-7,6-3 |
| ITF USA F1 | 2016/01/09 18:00 | Philip Bester v Clay Thompson | 6-3,6-3 |
| ITF USA F1 | 2016/01/08 18:00 | Ryan Shane v Philip Bester | 2-6,3-6 |
| Challenger Drummondville | 2016/03/15 20:35 | Omar Jasika v Roberto Ortega-Olmedo | 6-1,1-6,0-6 |
| ITF Portugal F1 | 2016/02/28 15:00 | Roberto Ortega-Olmedo v Jesse Huta Galung | 4-6,7-5,2-6 |
| ITF Portugal F1 | 2016/02/28 10:00 | Pablo Vivero Gonzalez v Roberto Ortega-Olmedo | 6-7,6-1,2-6 |
| ITF Portugal F1 | 2016/02/27 12:00 | Roberto Ortega-Olmedo v Hubert Hurkacz | 6-4,6-2 |
| ITF Portugal F1 | 2016/02/24 10:00 | Roberto Ortega-Olmedo v Andre Miele | 6-1,6-2 |
| ITF Egypt F4 | 2016/02/12 08:00 | N.Sriram Balaji v Roberto Ortega-Olmedo | 6-3,6-4 |
| ITF Egypt F4 | 2016/02/11 09:30 | Franjo Raspudic v Roberto Ortega-Olmedo | 4-6,6-7 |
| ITF Egypt F4 | 2016/02/10 09:55 | Matthias Wunner v Roberto Ortega-Olmedo | 5-7,3-6 |