Round: 26 Ground: Hardcourt indoor
| ITF Germany F15 | 2016/10/18 10:15 | Simon, Tobias v Tim Ruehl | 6-4,6-2 |
| ITF Germany F14 | 2016/10/12 15:25 | Simon, Tobias v Davydenko, Philipp | 6-7,6-7 |
| Challenger Mohammedia Qual | 2016/10/02 10:00 | Simon, Tobias v Maxime Janvier | 5-7,4-6 |
| Challenger Mohammedia Qual | 2016/10/01 15:10 | Simon, Tobias v Mies, Andreas | 4-6,7-6,6-2 |
| Challenger Mohammedia Qual | 2016/10/01 11:00 | Petrovic, Danilo v Simon, Tobias | 6-3,3-6,6-7 |
| ITF Spain F32 | 2016/09/27 13:15 | Simon, Tobias v Zhurbin, Alexander | 2-6,2-6 |
| ITF Spain F31 | 2016/09/21 15:00 | Jaume Munar v Simon, Tobias | 6-4,6-4 |
| ITF Italy F27 | 2016/09/01 11:30 | Simon, Tobias v Mesaros, Kristijan | 3-6,6-7 |
| ITF Germany F15 | 2016/10/19 08:00 | Prechtel, Sebastian v Hansen, Christian | 4-6,4-6 |
| ITF Germany F15 | 2016/10/17 08:00 | Hansen, Christian v Soltoianu, Andrei | 6-1,6-1 |
| ITF Germany F15 | 2016/10/15 08:00 | Prudnikau, Aliaksandr v Hansen, Christian | 4-6,1-6 |
| ITF Belgium F9 | 2016/08/06 13:35 | Hansen, Christian v Cloes, Loic | 6-4,6-2 |
| ITF Germany F9 | 2016/08/02 15:00 | Maden, Yannick v Hansen, Christian | 6-2,6-3 |
| ITF Germany F9 | 2016/08/01 08:00 | Benjamin Hassan v Hansen, Christian | 6-7,6-3,1-6 |