| ITF USA F22 | 2016/07/01 16:10 | Winston Lin v Connor Smith | 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 USA F22 | 2016/06/30 18:00 | Winston Lin v Andrew Carter | 6-4,6-2 |
| ITF Israel F11 | 2016/09/09 07:00 | Connor Smith v Evan Song | 6-1,6-1 |
| ITF Israel F11 | 2016/09/08 07:00 | Daniel Cukierman v Connor Smith | 4-6,2-6 |
| ITF Israel F11 | 2016/09/07 08:45 | Mor Bulis v Connor Smith | 5-7,2-6 |
| ITF Israel F11 | 2016/09/05 07:30 | Daniel Tamir v Connor Smith | 2-6,4-6 |
| ITF USA F27 | 2016/08/08 18:45 | Christian Harrison v Connor Smith | 6-3,7-5 |
| ITF USA F26 | 2016/08/03 16:00 | Connor Smith v Alfredo Perez | 6-2,4-6,1-6 |
| ITF USA F25 | 2016/07/29 14:00 | Connor Smith v Tennys Sandgren | 3-6,0-6 |
| ITF USA F25 | 2016/07/28 14:00 | Connor Smith v Roberto Quiroz | 6-1,6-4 |