Stadium: COURT 9 Round: 45 Ground: Hardcourt indoor
| ITF Canada F9 Qual | 2016/09/23 15:15 | Schnur, Brayden v Smith, Roy | 7-5,6-3 |
| ITF Canada F9 Qual | 2016/09/22 15:30 | Smith, Roy v Kaichi Uchida | 6-3,6-2 |
| ITF Canada F9 Qual | 2016/09/21 17:20 | Lin, Winston v Smith, Roy | 3-6,4-6 |
| ITF Canada F9 Qual | 2016/09/19 14:00 | Smith, Roy v Ochotta, Andrew | 6-3,6-3 |
| ITF Canada F9 Qual | 2016/09/18 16:00 | Ghader, Damien v Smith, Roy | 0-6,1-6 |
| ITF Canada F9 Qual | 2016/09/17 16:00 | Fortin, Michel-Alexandre v Smith, Roy | 4-6,2-6 |
| ITF Canada F8 Qual | 2016/09/11 13:00 | Smith, Roy v Becerra Jeria, Serge | 1-6,1-6 |
| ITF USA F27 Qual | 2016/08/07 13:30 | Escobar, Gonzalo v Smith, Roy | 6-1,6-0 |
| ITF USA F31 | 2016/10/16 17:00 | Spencer, Wil v Hiltzik, Aron | 6-4,6-3 |
| ITF USA F31 | 2016/10/15 15:00 | Nielsen, Frederik v Hiltzik, Aron | 5-7,4-6 |
| ITF USA F31 | 2016/10/14 15:00 | Hiltzik, Aron v Smith, Connor | 7-5,7-6 |
| ITF USA F31 | 2016/10/13 17:20 | Garanganga, Takanyi v Hiltzik, Aron | 2-6,5-7 |
| Columbus, USA, Qualifications | 2016/09/17 19:05 | Dominik Koepfer v Hiltzik, Aron | 3-6,7-6,6-2 |
| ITF Canada F6 | 2016/08/29 17:30 | Filip Peliwo v Hiltzik, Aron | 6-3,3-6,6-3 |
| ITF USA F27 | 2016/08/10 14:00 | Hiltzik, Jared v Hiltzik, Aron | 6-3,0-6,7-6 |
| ITF USA F27 | 2016/08/09 14:00 | Bradley, Julian v Hiltzik, Aron | 5-7,4-6 |