Round: 25 Ground: Hardcourt indoor
| ITF Canada F8 | 2016/09/15 15:55 | Winston Lin v Egor Koleganov | 6-4,6-2 |
| ITF Canada F8 | 2016/09/14 16:05 | Winston Lin v Serge Becerra | 5-7,6-1,6-0 |
| ITF Canada F8 | 2016/09/13 16:05 | Winston Lin v Hunter Reese | 6-7,6-3,6-4 |
| ITF Canada F7 | 2016/09/06 16:25 | Martin Beran v Winston Lin | 7-6,7-5 |
| ITF Finland F3 | 2016/08/14 22:00 | Winston Lin v Eero Vasa | 6-7,6-1,3-6 |
| ITF Finland F2 | 2016/08/09 07:30 | Winston Lin v Matvey Khomentovskiy | 4-6,2-6 |
| ITF Finland F1 | 2016/08/04 13:00 | Rubin Statham v Winston Lin | 6-4,6-0 |
| ITF Finland F1 | 2016/08/03 10:30 | Patrik Brydolf v Winston Lin | 6-7,2-6 |
| 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 |
| 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 |