Round: 25 Ground: Clay
| ITF USA F22 | 2016/07/01 16:10 | Winston Lin v Connor Smith | 6-3,6-4 |
| ITF Canada F9 Qual | 2016/09/21 17:20 | Winston Lin v Roy Smith | 3-6,4-6 |
| 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 Israel F13 | 2016/09/20 06:30 | Guy Michelevitz v Connor Smith | 4-6,4-6 |
| ITF Israel F12 | 2016/09/18 07:00 | Neil Pauffley v Connor Smith | 1-6,0-6 |
| ITF Israel F12 | 2016/09/17 07:00 | Connor Smith v Evan Song | 6-4,6-4 |
| ITF Israel F12 | 2016/09/16 07:00 | Jonathan Kanar v Connor Smith | 3-6,3-6 |
| ITF Israel F12 | 2016/09/15 07:00 | Dane Webb v Connor Smith | 1-6,1-6 |
| ITF Israel F12 | 2016/09/13 08:20 | Danny Thomas v Connor Smith | 6-3,5-7,3-6 |
| ITF Israel F11 | 2016/09/10 07:00 | Yannick Jankovits v Connor Smith | 6-7,3-6 |
| ITF Israel F11 | 2016/09/09 07:00 | Connor Smith v Evan Song | 6-1,6-1 |