Round: 44 Ground: Hardcourt indoor
| ITF Germany F16 | 2016/10/27 14:25 | Gijs Brouwer v George Von Massow | 6-4,6-2 |
| ITF Germany F16 | 2016/10/26 10:15 | Jordi Walder v George Von Massow | 3-6,6-3,6-7 |
| ITF Women Lagos | 2016/10/19 08:00 | George Von Massow v Ljubomir Celebic | 2-6,6-4,3-6 |
| ITF Croatia F10 | 2016/10/13 08:00 | Nerman Fatic v George Von Massow | 6-3,6-3 |
| ITF Croatia F10 | 2016/10/11 08:00 | Zvonimir Oreskovic v George Von Massow | 1-6,5-7 |
| Challenger Sibiu Qual | 2016/09/18 09:50 | Andreas Mies v George Von Massow | 6-4,6-1 |
| Challenger Sibiu Qual | 2016/09/18 01:04 | Andreas Mies v George Von Massow | 6-4,6-1 |
| Challenger Sibiu Qual | 2016/09/17 11:40 | George Von Massow v Adrian Bodmer | 6-3,6-2 |
| ITF Germany F17 | 2016/10/30 11:00 | Jan Simon Vrbsky v Stephan Gerritsen | 6-3,2-6,6-7 |
| ITF Germany F16 | 2016/10/26 09:00 | Lukas Ruepke v Stephan Gerritsen | 6-3,6-3 |
| ITF Hungary F6 | 2016/09/19 08:00 | Alen Avidzba v Stephan Gerritsen | 6-4,6-3 |
| ITF Hungary F6 | 2016/09/18 12:30 | Peter Balla v Stephan Gerritsen | 6-7,3-6 |
| ITF Netherlands F7 | 2016/08/30 12:05 | Guy Den Heijer v Stephan Gerritsen | 7-6,6-3 |
| ITF Netherlands F7 | 2016/08/28 10:00 | Stephan Gerritsen v Wilco Geenen | 6-2,6-0 |
| ITF Netherlands F6 | 2016/08/22 08:00 | Stephan Gerritsen v Eduardo Dischinger | 3-6,4-6 |
| ITF Netherlands F5 | 2016/08/18 13:20 | Altug Celikbilek v Stephan Gerritsen | 7-6,4-6,6-2 |