Round: 27 Ground: Clay
| ITF USA F37 | 2016/11/17 16:00 | Maxime Chazal v Patrick Kypson | 7-5,3-6,4-6 |
| ITF USA F37 | 2016/11/16 20:10 | Patrick Kypson v Gianni Ross | 6-4,6-3 |
| ITF USA F36 | 2016/11/08 15:30 | Patrick Kypson v Benjamin Sigouin | 7-6,1-6,4-6 |
| ITF USA F22 | 2016/06/29 17:30 | Patrick Kypson v Cameron Silverman | 3-6,3-6 |
| ITF Netherlands F1 | 2016/06/14 14:35 | Patrick Kypson v Jose Pereira | 0-6,2-6 |
| ITF Netherlands F1 Qual | 2016/06/11 08:00 | Lucas Andriamasilalao v Patrick Kypson | 1-6,2-6 |
| ITF USA F8 | 2016/02/25 16:00 | Patrick Kypson v Noah Rubin | 5-7,7-5,3-6 |
| ITF USA F8 | 2016/02/23 17:00 | Patricio Heras v Patrick Kypson | 2-6,7-5,3-6 |
| 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 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 |