Round: 25 Ground: Clay
| ITF Finland F2 Qual | 2016/08/07 11:30 | Esteban Bruna v Mika Kosonen | 5-7,5-7 |
| ITF Finland F2 Qual | 2016/08/06 10:00 | Esteban Bruna v Nicolas Bruna | 6-1,6-3 |
| ITF Latvia F1 | 2016/08/03 07:00 | Esteban Bruna v Tallon Griekspoor | 3-6,2-6 |
| ITF Estonia F1 | 2016/07/23 22:00 | Esteban Bruna v Tadas Tarasevicius | 6-2,4-6,5-7 |
| ITF Lithuania F1 | 2016/07/18 08:30 | Esteban Bruna v Mikalai Haliak | 3-6,1-6 |
| ITF Lithuania F1 | 2016/07/16 10:00 | Esteban Bruna v Karl Kiur Saar | 6-3,6-3 |
| ITF Germany F7 | 2016/07/10 08:00 | Esteban Bruna v Leonard Von Hindte | 2-6,2-6 |
| Challenger Bastad Qual | 2016/07/02 10:00 | Esteban Bruna v Lucas Renard | 0-6,2-6 |
| ITF Germany F8 | 2016/07/22 10:00 | Jose Hernandez-Fernandez v George Von Massow | 7-6,4-6,6-3 |
| ITF Germany F8 | 2016/07/21 10:50 | George Von Massow v Leon Schutt | 6-1,3-6,6-3 |
| ITF Germany F8 | 2016/07/19 10:00 | Thales Turini v George Von Massow | 3-6,4-6 |
| ITF Germany F8 Qual | 2016/07/18 10:00 | George Von Massow v Karlo Cubelic | 6-1,6-4 |
| ITF Germany F8 Qual | 2016/07/17 12:00 | George Von Massow v Phillip Schellhorn | 6-1,7-5 |
| ITF Germany F7 | 2016/07/12 09:00 | Maximilian Marterer v George Von Massow | 6-3,6-2 |
| ITF Germany F6 | 2016/07/07 10:00 | George Von Massow v Nik Razborsek | 4-6,6-4,2-6 |
| ITF Netherlands F3 | 2016/07/01 09:00 | Maxime Authom v George Von Massow | 3-6,6-2,6-3 |