Stadium: COURT 2 Round: 54 Ground: Clay
| Challenger Szczecin Qual | 2016/09/11 11:50 | George Von Massow v Wesley Koolhof | 7-6,3-6,6-4 |
| Challenger Alphen Qual | 2016/09/04 10:50 | George Von Massow v Marcin Gawron | 6-4,3-6,6-3 |
| ITF Germany F12 | 2016/08/24 08:00 | George Von Massow v Jean-Marc Werner | 2-6,0-6 |
| ITF Finland F3 | 2016/08/17 22:00 | Mikael Torpegaard v George Von Massow | 6-0,6-2 |
| ITF Finland F3 | 2016/08/16 22:00 | Herkko Pollanen v George Von Massow | 3-6,6-1,6-7 |
| ITF Finland F3 | 2016/08/15 22:00 | Esteban Bruna v George Von Massow | 2-6,3-6 |
| ITF Finland F2 | 2016/08/09 14:40 | George Von Massow v Patrik Rosenholm | 4-6,6-7 |
| ITF Germany F8 | 2016/07/22 10:00 | Jose Hernandez-Fernandez v George Von Massow | 7-6,4-6,6-3 |
| Challenger Szczecin Qual | 2016/09/11 11:55 | Vladimir Ivanov v Maxime Tabatruong | 4-6,6-2,6-4 |
| Challenger Szczecin Qual | 2016/09/10 13:15 | Filip Ambrozy v Vladimir Ivanov | 1-6,2-6 |
| Challenger Alphen Qual | 2016/09/04 13:30 | Vladimir Ivanov v Oscar Otte | 5-7,5-7 |
| ITF Russia F6 | 2016/08/18 07:00 | Alexander Igoshin v Vladimir Ivanov | 3-6,6-4,6-4 |
| ITF Russia F5 | 2016/08/14 07:00 | Evgeny Tyurnev v Vladimir Ivanov | 7-5,6-4 |
| ITF Russia F5 | 2016/08/13 07:00 | Matias Zukas v Vladimir Ivanov | 6-3,3-6,4-6 |
| ITF Russia F5 | 2016/08/12 07:00 | Vladimir Ivanov v Vitaly Kozyukov | 7-6,4-6,6-3 |
| ITF Russia F5 | 2016/08/11 09:30 | Vladimir Ivanov v Timur Kiyamov | 7-6,7-6 |