Round: 26 Ground: Hardcourt outdoor
| ITF USA F1 | 2016/01/10 19:00 | Stefan Kozlov v Philip Bester | 7-6,6-7,6-3 |
| 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 |
| ATP Newport | 2016/07/13 18:35 | Stefan Kozlov v Donald Young | 0-6,4-6 |
| ATP Newport | 2016/07/12 15:00 | Benjamin Becker v Stefan Kozlov | 1-6,2-6 |
| Wimbledon Qual | 2016/06/21 09:30 | Daniil Medvedev v Stefan Kozlov | 6-2,6-2 |
| Challenger Vicenza | 2016/05/27 13:40 | Stefan Kozlov v Edoardo Eremin | 1-6,6-3,3-6 |
| Challenger Vicenza | 2016/05/25 12:15 | Stefan Kozlov v Kimmer Coppejans | 6-4,6-4 |
| Challenger Vicenza | 2016/05/23 10:30 | Renzo Olivo v Stefan Kozlov | 3-6,4-6 |
| French Open Qual | 2016/05/16 10:40 | Grega Zemlja v Stefan Kozlov | 3-6,6-3,6-1 |
| Challenger Bordeaux Qual | 2016/05/08 10:10 | Jonathan Eysseric v Stefan Kozlov | 6-3,6-1 |