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