Round: 28 Ground: Clay
| 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 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 F37 | 2016/11/18 16:00 | Wil Spencer v Naoki Nakagawa | 6-3,3-6,2-6 |
| ITF USA F37 | 2016/11/17 16:00 | Naoki Nakagawa v Samuel Bensoussan | 6-1,0-6,6-3 |
| ITF USA F37 | 2016/11/16 17:00 | Naoki Nakagawa v Pirmin Haenle | 3-6,7-6,6-2 |
| ITF USA F35 | 2016/11/03 15:00 | Naoki Nakagawa v Wil Spencer | 6-3,5-7,2-6 |
| ITF USA F35 | 2016/11/01 16:25 | Sam Edwards v Naoki Nakagawa | 4-6,6-7 |
| ITF USA F34 | 2016/10/25 19:55 | Rubin Statham v Naoki Nakagawa | 6-1,6-7,6-3 |
| ITF USA F33 | 2016/10/20 17:00 | Lucas Gomez v Naoki Nakagawa | 6-2,7-6 |
| ITF USA F33 | 2016/10/18 21:40 | Naoki Nakagawa v Andrew Carter | 6-4,6-7,6-2 |