Round: 27 Ground: Hardcourt indoor
| ITF Bahrain F1 | 2016/04/01 11:00 | Yannick Maden v Tobias Simon | 6-4,6-4 |
| ATP Antwerp Qual | 2016/10/16 13:15 | Yannick Maden v Kimmer Coppejans | 6-2,6-3 |
| ATP Antwerp Qual | 2016/10/15 10:30 | Vincent Millot v Yannick Maden | 3-6,2-6 |
| ITF Italy F32 | 2016/10/08 08:30 | Yannick Maden v Stefano Travaglia | 2-6,6-4,6-3 |
| ITF Italy F32 | 2016/10/07 08:30 | Yannick Maden v Corentin Denolly | 6-2,6-0 |
| ITF Italy F32 | 2016/10/06 08:00 | Yannick Maden v Filippo Baldi | 6-4,6-2 |
| ITF Italy F32 | 2016/10/05 07:30 | Yannick Maden v Jacopo Stefanini | 6-3,6-0 |
| ITF Italy F32 | 2016/10/03 11:10 | Yannick Maden v Alexis Musialek | 6-1,6-3 |
| ITF Italy F31 | 2016/09/30 08:00 | Yannick Maden v Riccardo Bonadio | 3-6,6-7 |
| ITF Germany 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 Spain F32 | 2016/09/27 13:15 | Tobias Simon v Alexander Zhurbin | 2-6,2-6 |
| ITF Spain F31 | 2016/09/21 15:00 | Jaume Munar v Tobias Simon | 6-4,6-4 |
| ITF Italy F27 | 2016/09/01 11:30 | Tobias Simon v Kristijan Mesaros | 3-6,6-7 |
| ITF Italy F27 | 2016/08/31 13:55 | Pol Toledo Bague v Tobias Simon | 3-6,4-6 |