Round: 26 Ground: Hardcourt outdoor
| 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 USA F22 | 2016/07/02 14:00 | Winston Lin v Kaichi Uchida | 2-6,6-7 |
| ITF USA F22 | 2016/07/01 16:10 | Winston Lin v Connor Smith | 6-3,6-4 |
| ITF Canada F8 | 2016/09/13 18:15 | Serge Becerra v Malik Bhatnagar | 7-6,6-4 |
| ITF Canada F8 Qual | 2016/09/12 14:00 | Kazuma Kawachi v Serge Becerra | 1-6,3-6 |
| ITF Canada F8 Qual | 2016/09/11 13:00 | Roy Smith v Serge Becerra | 1-6,1-6 |
| ITF Canada F7 Qual | 2016/09/05 18:05 | Samuel Shropshire v Serge Becerra | 6-4,6-4 |
| ITF Canada F7 Qual | 2016/09/04 14:00 | Serge Becerra v Michael Genender | 6-4,6-2 |
| ITF Canada F6 | 2016/09/01 18:20 | Serge Becerra v Gonzales Austin | 0-6,3-6 |
| ITF Canada F6 | 2016/08/30 16:00 | Tyler Hochwalt v Serge Becerra | 6-7,2-6 |
| ITF USA F19 Qual | 2016/06/13 15:00 | Serge Becerra v Logan Smith | 6-3,2-6,6-3 |