Round: 25 Ground: Clay
| ITF Germany F4 | 2016/06/21 13:35 | Arvidsson, Isak v von Massow, George | 6-2,6-3 |
| ITF Poland F4 | 2016/06/13 11:00 | von Massow, George v Panfil, Grzegorz | 6-7,2-6 |
| Italie F8, Qualifications Simples | 2016/04/25 08:00 | Corentin Moutet v von Massow, George | 6-0,6-4 |
| ITF Greece F4 | 2016/04/12 07:00 | von Massow, George v Lescure, Mick | 6-4,4-6,4-6 |
| ITF Greece F3 | 2016/04/05 08:30 | von Massow, George v Arvidsson, Isak | 5-7,3-6 |
| ITF Greece F2 | 2016/03/31 07:00 | Jankovic, Miki v von Massow, George | 6-4,3-6,7-6 |
| ITF Greece F2 | 2016/03/29 13:00 | Appelgren, Daniel v von Massow, George | 6-7,2-6 |
| ITF Greece F1 | 2016/03/24 09:30 | Safranek, Vaclav v von Massow, George | 6-4,7-6 |
| ITF Poland F4 | 2016/06/14 08:00 | Dembek, Michal v Raab, Demian | 7-6,6-2 |
| ITF Poland F3 | 2016/06/07 14:00 | Kamil Majchrzak v Raab, Demian | 6-1,6-7,6-3 |
| ITF Poland F2 | 2016/06/01 09:25 | Kapas, Andriej v Raab, Demian | 6-3,6-2 |
| ITF Italy F7 | 2016/04/18 09:45 | Raab, Demian v Leonardi, Filippo | 2-6,1-6 |
| ITF Italy F6 | 2016/04/12 07:30 | Raab, Demian v Grigelis, Laurynas | 1-6,6-4,2-6 |
| ITF Turkey F11 | 2016/03/18 08:00 | Raab, Demian v Fortuna, Claudio | 1-6,0-6 |
| ITF Turkey F11 | 2016/03/17 08:00 | Granollers, Gerard v Raab, Demian | 3-6,2-6 |
| ITF Turkey F11 | 2016/03/16 09:25 | Raab, Demian v Bogdan Bobrov | 6-4,6-3 |