Round: 45 Ground: Hardcourt outdoor
| ITF Canada F9 Qual | 2016/09/21 14:00 | Adam El Mihdawy v Andrew Carter | 6-1,6-1 |
| Challenger Cary Qual | 2016/09/12 16:00 | Ryan Haviland v Andrew Carter | 6-2,6-2 |
| Challenger Cary Qual | 2016/09/11 14:00 | Andrew Carter v Jared Hiltzik | 7-6,3-6,7-5 |
| Challenger Cary Qual | 2016/09/10 15:50 | Andrew Carter v Dennis Uspensky | 6-2,6-4 |
| ITF Canada F7 | 2016/09/06 17:35 | Andrew Carter v Philip Bester | 3-6,2-6 |
| ITF Canada F6 | 2016/09/02 19:00 | Brayden Schnur v Andrew Carter | 7-5,6-2 |
| ITF Canada F6 | 2016/08/31 16:30 | Andrew Carter v Brandon L. Sutter | 6-4,6-2 |
| ITF Canada F6 | 2016/08/29 16:00 | Andrew Carter v Michael Zhu | 3-6,6-3,6-1 |
| Challenger Columbus | 2016/09/20 15:00 | Roberto Quiroz v Brydan Klein | 6-4,6-2 |
| Challenger Cary | 2016/09/14 17:00 | Dennis Novikov v Brydan Klein | 6-4,6-4 |
| Challenger Cary | 2016/09/12 17:30 | Brydan Klein v Sekou Bangoura | 1-6,7-5,6-2 |
| Challenger Granby | 2016/08/02 19:45 | Brydan Klein v Gregoire Barrere | 3-6,3-6 |
| ATP Newport Qual | 2016/07/11 16:25 | Brydan Klein v Brian Baker | 6-7,4-6 |
| ATP Newport Qual | 2016/07/10 19:45 | Brydan Klein v Michael Mmoh | 7-6,6-2 |
| Wimbledon | 2016/06/27 13:15 | Brydan Klein v Nicolas Mahut | 6-7,4-6,4-6 |
| French Open Qual | 2016/05/17 09:25 | Sergiy Stakhovsky v Brydan Klein | 6-3,6-3 |