Stadium: STADIUM Round: 26 Ground: Hardcourt outdoor
| Challenger Tiburon Qual | 2016/09/24 17:00 | Carter, Andrew v Klein, Brydan | 6-4,2-6,1-6 |
| Challenger Stockton Qual | 2016/10/01 17:00 | Krajicek, Austin v Klein, Brydan | 5-7,6-2,2-6 |
| Challenger Tiburon Qual | 2016/09/26 17:00 | Reid, Matt v Klein, Brydan | 3-6,5-7 |
| Challenger Tiburon Qual | 2016/09/25 19:25 | Farren, Connor v Klein, Brydan | 1-6,1-6 |
| Challenger Tiburon Qual | 2016/09/24 17:00 | Carter, Andrew v Klein, Brydan | 6-4,2-6,1-6 |
| Challenger Columbus | 2016/09/20 15:00 | Quiroz, Roberto v Klein, Brydan | 6-4,6-2 |
| Challenger Cary | 2016/09/14 17:00 | Novikov, Dennis v Klein, Brydan | 6-4,6-4 |
| Challenger Cary | 2016/09/12 17:30 | Klein, Brydan v Bangoura, Sekou | 1-6,7-5,6-2 |
| Challenger Granby | 2016/08/02 19:45 | Klein, Brydan v Gregoire Barrere | 3-6,3-6 |
| Challenger Stockton Qual | 2016/10/01 17:00 | Carter, Andrew v Martinez, Luis David | 0-6,7-6,6-1 |
| Challenger Tiburon Qual | 2016/09/24 17:00 | Carter, Andrew v Klein, Brydan | 6-4,2-6,1-6 |
| ITF Canada F9 Qual | 2016/09/21 14:00 | El Midhawy, Adam v Carter, Andrew | 6-1,6-1 |
| Challenger Cary Qual | 2016/09/12 16:00 | Ryan Haviland v Carter, Andrew | 6-2,6-2 |
| Challenger Cary Qual | 2016/09/11 14:00 | Carter, Andrew v Hiltzik, Jared | 7-6,3-6,7-5 |
| Challenger Cary Qual | 2016/09/10 15:50 | Carter, Andrew v Uspensky, Dennis | 6-2,6-4 |
| Canada F7, Singles | 2016/09/06 17:35 | Carter, Andrew v Bester, Philip | 3-6,2-6 |
| ITF Canada F6 | 2016/09/02 19:00 | Schnur, Brayden v Carter, Andrew | 7-5,6-2 |