Stadium: COURT 9 Round: 45 Ground: Hardcourt indoor
| ITF Canada F9 Qual | 2016/09/23 15:15 | Brayden Schnur v Roy Smith | 7-5,6-3 |
| 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 F31 | 2016/10/16 17:00 | Wil Spencer v Aron Hiltzik | 6-4,6-3 |
| ITF USA F31 | 2016/10/15 15:00 | Frederik Nielsen v Aron Hiltzik | 5-7,4-6 |
| ITF USA F31 | 2016/10/14 15:00 | Aron Hiltzik v Connor Smith | 7-5,7-6 |
| ITF USA F31 | 2016/10/13 17:20 | Takanyi Garanganga v Aron Hiltzik | 2-6,5-7 |
| Challenger Columbus Qual | 2016/09/17 19:05 | Dominik Koepfer v Aron Hiltzik | 3-6,7-6,6-2 |
| ITF Canada F6 | 2016/08/29 17:30 | Filip Peliwo v Aron Hiltzik | 6-3,3-6,6-3 |
| ITF USA F27 | 2016/08/10 14:00 | Jared Hiltzik v Aron Hiltzik | 6-3,0-6,7-6 |
| ITF USA F27 | 2016/08/09 14:00 | Julian Bradley v Aron Hiltzik | 5-7,4-6 |