Round: 44 Ground: Hardcourt indoor
| 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 F27 Qual | 2016/08/06 13:30 | Smith, Roy v Colin Markes | 6-3,6-4 |
| USA F26, Singles Qualifying | 2016/07/30 15:00 | Smith, Roy v Perez, Alfredo | 6-7,1-6 |
| ITF USA F25 Qual | 2016/07/24 13:15 | Smith, Roy v Ignat, Dragos Constantin | 6-7,1-6 |
| ITF USA F25 Qual | 2016/07/23 13:30 | Smith, Roy v Seidman, Jason | 6-1,6-1 |
| ITF Canada F8 Qual | 2016/09/11 13:00 | Hu, Nicholas S v Ochotta, Andrew | 6-3,6-1 |
| ITF Canada F6 | 2016/08/29 17:45 | Ochotta, Andrew v Stefanos Tsitsipas | 1-6,3-6 |
| Challenger Granby Qual | 2016/07/31 19:40 | Emilio Gomez v Ochotta, Andrew | 6-1,6-0 |
| Challenger Granby Qual | 2016/07/30 16:00 | Dynka, Tom v Ochotta, Andrew | 3-6,3-6 |
| ITF Canada F4 Qual | 2016/06/26 19:00 | Ochotta, Andrew v Korinek, Andrew | 4-6,3-6 |
| ITF Canada F3 Qual | 2016/06/19 22:00 | Ochotta, Andrew v Manji, Raheel | 1-6,4-6 |
| ITF USA F34 Qual | 2015/11/22 16:00 | Ochotta, Andrew v Sude, Jakob | 0-6,1-6 |
| ITF Canada F8 | 2015/09/01 17:10 | Smith, Raleigh v Ochotta, Andrew | 6-3,6-2 |