Round: 26 Ground: Clay
| ITF Germany F9 | 2016/08/02 11:00 | Naoki Nakagawa v Rudolf Molleker | 4-6,7-6,6-1 |
| Challenger Cali 2 Qual | 2016/07/03 21:10 | Tomas Barrios Vera v Naoki Nakagawa | 7-5,6-1 |
| Challenger Cali 2 Qual | 2016/07/03 15:50 | Naoki Nakagawa v Juan Manuel Lopez | 6-2,6-1 |
| ITF Colombia F3 | 2016/06/28 14:30 | Naoki Nakagawa v Matias Zukas | 3-6,4-6 |
| ITF Colombia F3 Qual | 2016/06/27 19:10 | Naoki Nakagawa v Jose Antonio Rodriguez Rodriguez | 6-4,6-2 |
| ITF Colombia F3 Qual | 2016/06/26 18:00 | Naoki Nakagawa v Barlaham Zuluaga Gaviria | 7-5,7-6 |
| ITF Colombia F2 | 2016/06/22 15:00 | Roberto Quiroz v Naoki Nakagawa | 6-7,6-3,6-2 |
| ITF Colombia F2 | 2016/06/21 18:20 | Daniel Mora v Naoki Nakagawa | 0-6,1-6 |
| ITF Germany F9 | 2016/08/02 11:55 | Alex Solanki v Christopher Heyman | 4-6,0-6 |
| ITF France F15 | 2016/07/20 15:30 | Christopher Heyman v Gibril Diarra | 7-5,4-6,5-7 |
| ITF France F15 | 2016/07/19 14:15 | Christopher Heyman v Matteo Martineau | 6-2,6-4 |
| ITF Netherlands F4 | 2016/07/08 09:00 | Botic Van De Zandschulp v Christopher Heyman | 6-3,6-3 |
| ITF Netherlands F4 | 2016/07/05 13:30 | Robert Willekes MacDonald v Christopher Heyman | 0-6,5-7 |
| ITF Germany F5 | 2016/07/03 09:00 | Antoine Hoang v Christopher Heyman | 7-6,2-6,6-7 |
| ITF Germany F5 | 2016/07/02 11:35 | Marcin Gawron v Christopher Heyman | 3-6,3-6 |
| ITF Germany F5 | 2016/07/01 16:10 | Jonas Luetjen v Christopher Heyman | 6-7,3-6 |