Round: 26 Ground: Clay
| ITF USA F37 | 2016/11/16 17:00 | Naoki Nakagawa v Haenle, Pirmin | 3-6,7-6,6-2 |
| ITF USA F35 | 2016/11/03 15:00 | Naoki Nakagawa v Spencer, Wil | 6-3,5-7,2-6 |
| ITF USA F35 | 2016/11/01 16:25 | Edwards, Sam v Naoki Nakagawa | 4-6,6-7 |
| USA F34, Singles | 2016/10/25 19:55 | Rubin Statham v Naoki Nakagawa | 6-1,6-7,6-3 |
| USA F33, Singles | 2016/10/20 17:00 | Gomez, Lucas v Naoki Nakagawa | 6-2,7-6 |
| USA F33, Singles | 2016/10/18 21:40 | Naoki Nakagawa v Carter, Andrew | 6-4,6-7,6-2 |
| Spain F30, Singles | 2016/09/14 09:55 | Naoki Nakagawa v Bernabe Zapata Miralles | 4-6,3-6 |
| Spain F30, Singles | 2016/09/13 07:30 | Milovic, Zeljko v Naoki Nakagawa | 5-7,5-7 |
| ITF USA F37 | 2016/11/16 17:30 | Cotrone, Dominic v Bensoussan, Samuel | 3-6,5-7 |
| ITF USA F36 | 2016/11/10 18:15 | Roberto Cid Subervi v Bensoussan, Samuel | 3-6,7-6,6-4 |
| ITF USA F36 | 2016/11/09 16:00 | Webb, Dane v Bensoussan, Samuel | 4-6,7-5,3-6 |
| ITF USA F35 | 2016/11/05 15:00 | Benitez Chavarriaga, Juan Manuel v Bensoussan, Samuel | 6-0,4-6,6-3 |
| ITF USA F35 | 2016/11/04 16:20 | Bensoussan, Samuel v Spencer, Wil | 4-6,6-2,6-4 |
| ITF USA F35 | 2016/11/03 15:00 | Dougaz, Aziz v Bensoussan, Samuel | 3-6,3-6 |
| ITF USA F35 | 2016/11/02 17:20 | Slobodchikov, Ronald v Bensoussan, Samuel | 3-6,2-6 |
| ITF Italy F34 | 2016/10/20 09:55 | Matteo Berrettini v Bensoussan, Samuel | 6-2,6-3 |