| ITF Canada F9 Qual | 2016/09/21 17:20 | Winston Lin v Roy Smith | 3-6,4-6 |
| ITF USA F5 | 2017/01/23 15:00 | Ilya Vasilyev v Winston Lin | 5-7,7-5,6-4 |
| ITF USA F5 | 2017/01/22 15:00 | Joel Vincent Link v Winston Lin | 4-6,2-6 |
| ITF USA F5 | 2017/01/21 18:00 | Junior Alexander Ore v Winston Lin | 2-6,6-2,2-6 |
| 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 Puerto Rico F1 | 2016/12/21 15:10 | Benjamin Lock v Roy Smith | 6-1,6-4 |
| ITF Puerto Rico F1 | 2016/12/19 14:00 | Courtney John Lock v Roy Smith | 6-7,3-6 |
| ITF USA F40 Qual | 2016/12/05 18:00 | JC Aragone v Roy Smith | 6-1,6-1 |
| Challenger Columbus 2 Qual | 2016/11/19 16:40 | Damon Gooch v Roy Smith | 6-1,6-2 |
| Challenger Charlottesville Qual | 2016/10/29 17:40 | Roy Smith v Aron Hiltzik | 4-6,2-6 |
| ITF Canada F9 Qual | 2016/09/23 15:15 | Brayden Schnur v Roy Smith | 7-5,6-3 |
| ITF Canada F9 Qual | 2016/09/22 15:30 | Roy Smith v Kaichi Uchida | 6-3,6-2 |
| ITF Canada F9 Qual | 2016/09/21 17:20 | Winston Lin v Roy Smith | 3-6,4-6 |