Round: 25 Ground: Carpet indoor
| 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 Italy F27 | 2016/08/31 13:55 | Toledo Bague, Pol v Simon, Tobias | 3-6,4-6 |
| ITF Italy F27 | 2016/08/29 09:00 | Simon, Tobias v Roberto, Riccardo | 6-1,6-2 |
| ITF France F7 | 2016/03/23 14:45 | Sidorenko, Alexandre v Davydenko, Philipp | 6-4,6-4 |
| ITF France F7 | 2016/03/21 10:00 | Kern, Robin v Davydenko, Philipp | 6-7,1-6 |
| Egypt F6, Singles Qualifying | 2016/02/25 10:00 | Davydenko, Philipp v Gleb Sakharov | 1-6,3-6 |
| Egypt F6, Singles Qualifying | 2016/02/23 08:00 | Davydenko, Philipp v Denis Yevseyev | 6-4,6-2 |
| Egypt F5, Singles Qualifying | 2016/02/17 11:00 | Davydenko, Philipp v Gleb Sakharov | 4-6,5-7 |
| ITF Egypt F4 | 2016/02/11 08:00 | Davydenko, Philipp v Lloyd Harris | 6-7,3-6 |
| ITF Egypt F4 | 2016/02/09 10:40 | Davydenko, Philipp v Oleg Prihodko | 7-6,3-6,6-3 |
| Challenger Szczecin Qual | 2015/09/13 09:00 | Davydenko, Philipp v Maciej Rajski | 6-4,4-6,4-6 |