Round: 44 Ground: Hardcourt indoor
| ITF Canada F8 Qual | 2016/09/11 13:00 | Rached Rihani v Michel-Alexandre Fortin | 6-1,6-4 |
| 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 |
| ITF USA F26 Qual | 2016/07/30 15:00 | Roy Smith v Alfredo Perez | 6-7,1-6 |
| ITF USA F25 Qual | 2016/07/24 13:15 | Roy Smith v Dragos Constantin Ignat | 6-7,1-6 |
| ITF USA F25 Qual | 2016/07/23 13:30 | Roy Smith v Jason Seidman | 6-1,6-1 |
| ITF USA F24 Qual | 2016/07/16 15:00 | Roy Smith v Andrew Watson | 2-6,1-6 |
| ITF USA F23 Qual | 2016/06/25 15:30 | Michael Riechmann v Roy Smith | 3-6,6-4,7-5 |