Round: 27 Ground: Hardcourt indoor
| ITF Canada F9 Qual | 2016/09/22 15:45 | Brayden Schnur v David Volfson | 6-2,6-3 |
| ITF Canada F9 Qual | 2016/09/20 15:45 | Brayden Schnur v Chandril Sood | 6-1,6-2 |
| Challenger Cary | 2016/09/16 17:45 | Brayden Schnur v James McGee | 2-6,4-6 |
| Challenger Cary | 2016/09/15 23:30 | Brayden Schnur v Eric Quigley | 7-6,6-1 |
| Challenger Cary | 2016/09/14 00:45 | Austin Krajicek v Brayden Schnur | 6-7,5-7 |
| ITF Canada F6 | 2016/09/04 18:00 | Brayden Schnur v Tim Van Rijthoven | 6-3,3-6,6-3 |
| ITF Canada F6 | 2016/09/03 18:00 | Philip Bester v Brayden Schnur | 4-6,6-3,3-6 |
| ITF Canada F6 | 2016/09/02 19:00 | Brayden Schnur v Andrew Carter | 7-5,6-2 |
| ITF Canada F9 Qual | 2016/09/22 15:30 | Roy Smith v Kaichi Uchida | 6-3,6-2 |
| ITF Canada F9 Qual | 2016/09/21 17:20 | Winston Lin v Roy Smith | 3-6,4-6 |
| ITF Canada F9 Qual | 2016/09/19 14:00 | Roy Smith v Andrew Ochotta | 6-3,6-3 |
| ITF Canada F9 Qual | 2016/09/18 16:00 | Damien Ghader v Roy Smith | 0-6,1-6 |
| ITF Canada F9 Qual | 2016/09/17 16:00 | Michel-Alexandre Fortin v Roy Smith | 4-6,2-6 |
| ITF Canada F8 Qual | 2016/09/11 13:00 | Roy Smith v Serge Becerra | 1-6,1-6 |
| ITF USA F27 Qual | 2016/08/07 13:30 | Gonzalo Escobar v Roy Smith | 6-1,6-0 |
| ITF USA F27 Qual | 2016/08/06 13:30 | Roy Smith v Colin Markes | 6-3,6-4 |