Round: 25 Ground: Hardcourt outdoor
| 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 Kitzbuhel Qual | 2016/07/16 09:00 | Nils Langer v Filippo Volandri | 1-6,6-2,6-7 |
| Challenger San Benedetto | 2016/07/11 18:40 | Nils Langer v Ivan Nedelko | 3-6,6-1,2-6 |
| Challenger Marburg | 2016/06/28 10:40 | Nils Langer v Daniel Gimeno-Traver | 6-7,7-5,1-6 |
| Wimbledon Qual | 2016/06/21 11:15 | Igor Sijsling v Nils Langer | 6-2,6-4 |
| Challenger Poprad Tatry | 2016/06/14 11:20 | Nils Langer v Andrej Martin | 5-7,7-6,2-6 |
| French Open Qual | 2016/05/17 08:00 | Nils Langer v Andrej Martin | 3-6,1-6 |
| ATP Munich Qual | 2016/04/24 12:45 | Nils Langer v Cedrik-Marcel Stebe | 6-2,6-7,4-6 |
| ATP Munich Qual | 2016/04/23 13:05 | Mirza Basic v Nils Langer | 4-6,3-6 |