Round: 25 Ground: Clay
| ITF Canada F2 | 2015/03/11 22:00 | Philip Bester v Victor Krustev | 6-1,6-2 |
| ITF USA F13 | 2016/04/15 20:00 | Philip Bester v Dennis Nevolo | 0-6,1-6 |
| ITF USA F13 | 2016/04/14 15:00 | Philip Bester v Hans Hach Verdugo | 6-1,6-1 |
| ITF USA F13 | 2016/04/13 20:00 | Philip Bester v Felipe Mantilla | 7-5,6-2 |
| 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 Kupa | 2016/03/06 15:15 | Richard Gasquet v Philip Bester | 6-1,7-6 |
| ITF USA F16 | 2016/05/02 13:30 | Robert Levine v Victor Krustev | 6-2,4-6,1-6 |
| ITF USA F15 Qual | 2016/04/24 17:00 | Michael Lippens v Victor Krustev | 6-3,6-7,7-6 |
| ITF USA F15 Qual | 2016/04/23 18:00 | Bradley Holt v Victor Krustev | 2-6,7-5,6-7 |
| ITF USA F15 Qual | 2016/04/22 17:30 | Victor Krustev v Esteban Bruna | 6-4,6-2 |
| ITF USA F14 | 2016/04/18 14:30 | Victor Krustev v Jonathan Chang | 4-6,2-6 |
| ITF USA F14 | 2016/04/17 17:00 | Sergey Belov v Victor Krustev | 4-6,6-2,1-6 |
| Challenger Drummondville Qual | 2016/03/13 19:30 | Victor Krustev v Nicolas Jarry | 1-6,2-6 |
| Challenger Drummondville Qual | 2016/03/12 20:05 | Victor Krustev v Joshua Peck | 6-4,3-6,6-3 |