Round: 28 Ground: Clay
| ITF Germany F9 | 2016/08/04 13:40 | Yannick Maden v Marvin Netuschil | 6-2,2-6,6-2 |
| ITF Germany F9 | 2016/08/04 09:00 | Yannick Maden v Oscar Otte | 6-3,6-3 |
| ITF Germany F9 | 2016/08/02 15:00 | Yannick Maden v Christian Hansen | 6-2,6-3 |
| ITF Germany F4 | 2016/06/26 07:30 | Yannick Maden v Jonas Luetjen | 6-0,4-6,6-1 |
| ITF Germany F4 | 2016/06/24 13:00 | Yannick Maden v Gabor Borsos | 6-4,6-2 |
| ITF Germany F4 | 2016/06/23 15:00 | Yannick Maden v Frederik Press | 6-2,6-3 |
| ITF Germany F4 | 2016/06/22 15:10 | Yannick Maden v Niclas Braun | 6-0,6-2 |
| Challenger Perugia | 2016/06/15 09:00 | Yannick Maden v Blaz Rola | 6-2,5-7,6-7 |
| ITF Germany F9 | 2016/08/04 14:00 | Johann Willems v Naoki Nakagawa | 7-5,5-7,6-7 |
| ITF Germany F9 | 2016/08/03 10:00 | Naoki Nakagawa v Christopher Heyman | 6-4,2-6,7-5 |
| 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 |