Round: 25 Ground: Hardcourt outdoor
| ITF Italy F32 | 2015/10/22 14:00 | Ljubomir Celebic v George Von Massow | 4-6,6-7 |
| 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 |
| Challenger Szczecin Qual | 2016/09/12 12:10 | George Von Massow v Vladimir Ivanov | 6-7,6-2,2-6 |
| Challenger Szczecin Qual | 2016/09/11 11:50 | George Von Massow v Wesley Koolhof | 7-6,3-6,6-4 |
| Challenger Alphen Qual | 2016/09/04 10:50 | George Von Massow v Marcin Gawron | 6-4,3-6,6-3 |
| ITF Australia F8 | 2016/10/11 10:30 | Ljubomir Celebic v Paul Woerner | 7-5,6-2 |
| ITF Croatia F9 | 2016/10/08 11:00 | Ljubomir Celebic v Riccardo Bellotti | 6-4,0-6,5-7 |
| Australian Open | 2016/10/07 15:00 | Ljubomir Celebic v Tim Van Terheijden | 6-2,7-6 |
| ITF Croatia F9 | 2016/10/06 08:00 | Ljubomir Celebic v Pascal Meis | 6-3,5-7,7-5 |
| ITF Italy F32 | 2016/10/04 08:00 | Ljubomir Celebic v Daniele Capecchi | 6-0,6-0 |
| ITF Serbia F6 | 2016/09/10 08:00 | Borna Gojo v Ljubomir Celebic | 7-5,6-7,0-6 |
| ITF Serbia F6 | 2016/09/09 09:25 | Davide Galoppini v Ljubomir Celebic | 0-6,2-6 |
| ITF Serbia F6 | 2016/09/08 07:45 | Lukas Vejvara v Ljubomir Celebic | 3-6,4-6 |