| 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 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 USA F25 Qual | 2016/07/24 13:15 | Justin Roberts v Dane Webb | 4-6,6-1,3-6 |
| ITF Canada F5 | 2016/07/07 20:20 | Justin Roberts v Brayden Schnur | 2-6,3-6 |
| ITF Canada F5 | 2016/07/05 17:30 | Mesa Mei v Justin Roberts | 5-7,2-6 |
| ITF Canada F5 Qual | 2016/07/02 19:30 | Justin Roberts v Nicholas Kamisar | 6-2,6-3 |
| ITF USA F20 Qual | 2016/06/20 17:00 | Justin Roberts v Evan Zhu | 3-6,6-3,3-6 |
| ITF USA F20 Qual | 2016/06/19 17:00 | Justin Roberts v Drew Van Orderlain | 7-6,6-3 |
| ITF USA F19 | 2016/06/16 15:00 | Justin Roberts v Hans Hach Verdugo | 2-6,6-4,3-6 |
| ITF USA F19 Qual | 2016/06/13 15:00 | Justin Roberts v Ryoto Tachi | 6-1,6-2 |