Round: 25 Ground: Clay
| ITF USA F31 | 2016/10/13 15:00 | Winston Lin v Connor Smith | 2-6,6-7 |
| ITF USA F22 | 2016/07/01 16:10 | Winston Lin v Connor Smith | 6-3,6-4 |
| ITF USA F40 | 2016/12/08 17:10 | Dominik Koepfer v Winston Lin | 6-4,4-6,6-4 |
| ITF USA F37 | 2016/11/18 16:00 | Patrick Kypson v Winston Lin | 6-7,7-6,6-1 |
| ITF USA F37 | 2016/11/17 17:30 | Nathaniel Lammons v Winston Lin | 4-6,4-6 |
| ITF USA F36 | 2016/11/08 15:30 | Winston Lin v Justin Roberts | 6-7,4-6 |
| ITF USA F32 | 2016/10/19 18:45 | Winston Lin v Guanarteme N Delgado | 0-6,2-6 |
| ITF USA F31 | 2016/10/13 15:00 | Winston Lin v Connor Smith | 2-6,6-7 |
| ITF USA F31 | 2016/10/11 15:00 | Julian Lenz v Winston Lin | 3-6,6-4,2-6 |
| ITF Canada F9 Qual | 2016/09/21 17:20 | Winston Lin v Roy Smith | 3-6,4-6 |
| ITF Costa Rica F1 | 2016/11/10 18:40 | Connor Smith v Danny Thomas | 2-6,6-4,4-6 |
| ITF Costa Rica F1 | 2016/11/09 17:45 | Connor Smith v Brian Cernoch | 6-2,6-3 |
| ITF Costa Rica F1 | 2016/11/07 17:15 | Connor Smith v Wilfredo Gonzalez | 7-5,3-6,6-4 |
| ITF USA F33 | 2016/10/20 19:25 | Connor Smith v Marcos Giron | 5-7,4-6 |
| ITF USA F33 | 2016/10/18 20:00 | Connor Smith v Michail Pervolarakis | 6-3,6-3 |
| ITF USA F31 | 2016/10/14 15:00 | Aron Hiltzik v Connor Smith | 7-5,7-6 |
| ITF USA F31 | 2016/10/13 15:00 | Winston Lin v Connor Smith | 2-6,6-7 |
| ITF USA F31 | 2016/10/11 17:50 | Eric Rutledge v Connor Smith | 0-6,4-6 |