Round: 27 Ground: Hardcourt indoor
| ITF Bahrain F1 | 2016/04/01 11:00 | Yannick Maden v Tobias Simon | 6-4,6-4 |
| ITF Great Britain F4 | 2016/10/27 12:40 | Yannick Maden v Zizou Bergs | 6-4,6-7,6-2 |
| ITF Great Britain F4 | 2016/10/26 10:30 | Yannick Maden v Finn Bass | 6-4,6-2 |
| ATP Antwerp | 2016/10/19 11:50 | Gilles Simon v Yannick Maden | 6-3,6-2 |
| 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 Great Britain F4 | 2016/10/27 13:00 | Jay Clarke v Tobias Simon | 4-6,4-6 |
| ITF Great Britain F4 | 2016/10/26 11:20 | Mateusz Terczynski v Tobias Simon | 6-7,2-6 |
| ITF Germany F15 | 2016/10/23 12:10 | Tobias Simon v Marek Jaloviec | 5-7,6-7 |
| ITF Germany F15 | 2016/10/21 14:35 | Tobias Simon v Gijs Brouwer | 7-6,6-2 |
| ITF Germany F15 | 2016/10/20 14:10 | Tobias Simon v Christian Hansen | 6-1,7-6 |
| ITF Germany F15 | 2016/10/18 10:15 | Tobias Simon v Tim Ruehl | 6-4,6-2 |
| 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 |