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