Round: 25 Ground: Clay
| Germany F8, Singles | 2016/07/22 10:00 | Hernandez-Fernandez, Jose v von Massow, George | 7-6,4-6,6-3 |
| Germany F8, Singles | 2016/07/21 10:50 | von Massow, George v Schutt, Leon | 6-1,3-6,6-3 |
| Germany F8, Singles | 2016/07/19 10:00 | Turini, Thales v von Massow, George | 3-6,4-6 |
| ITF Germany F8 Qual | 2016/07/18 10:00 | von Massow, George v Karlo Cubelic | 6-1,6-4 |
| ITF Germany F8 Qual | 2016/07/17 12:00 | von Massow, George v Schellhorn, Phillip | 6-1,7-5 |
| ITF Germany F7 | 2016/07/12 09:00 | Maximilian Marterer v von Massow, George | 6-3,6-2 |
| ITF Germany F6 | 2016/07/07 10:00 | von Massow, George v Nik Razborsek | 4-6,6-4,2-6 |
| ITF Netherlands F3 | 2016/07/01 09:00 | Authom, Maxime v von Massow, George | 3-6,6-2,6-3 |
| Challenger Prague 2 | 2016/07/24 10:40 | Vadym Ursu v Rosenholm, Patrik | 4-6,6-2,7-6 |
| Challenger Prague 2 | 2016/07/23 11:50 | Sproch, Dominik v Rosenholm, Patrik | 3-6,4-6 |
| ITF Belgium F5 | 2016/07/15 08:00 | Michael Geerts v Rosenholm, Patrik | 6-2,5-7,6-0 |
| ITF Belgium F5 | 2016/07/12 12:10 | Terczynski, Mateusz v Rosenholm, Patrik | 4-6,6-3,1-6 |
| Challenger Bastad Qual | 2016/07/02 12:20 | Rosenholm, Patrik v Appelgren, Daniel | 6-7,6-7 |
| Italie F32, Simples | 2016/05/17 09:50 | Christopher O'Connell v Rosenholm, Patrik | 4-6,6-3,6-2 |
| Italie F32, Simples | 2016/05/12 08:00 | Omar Jasika v Rosenholm, Patrik | 6-3,6-1 |
| Italie F32, Simples | 2016/05/11 13:50 | Jonathan Mridha v Rosenholm, Patrik | 2-6,3-6 |