Round: 25 Ground: Clay
| ITF Serbia F3 | 2016/08/03 08:00 | Gabriel Donev v Petar Conkic | 2-6,6-3,2-6 |
| ITF Serbia F3 Qual | 2016/08/01 08:00 | Gabriel Donev v Danylo Veremeychuk | 4-6,6-1,7-5 |
| ITF Serbia F3 Qual | 2016/07/31 07:00 | Gabriel Donev v Aleksandar Jocic | 6-0,6-1 |
| ITF Macedonia F2 | 2016/06/28 09:25 | Gabriel Donev v Tomislav Jotovski | 4-6,1-6 |
| ITF Macedonia F2 | 2016/06/27 09:10 | Gabriel Donev v Yasha Zemel | 6-7,6-1,6-4 |
| ITF Macedonia F2 | 2016/06/26 14:00 | Gabriel Donev v Milos Nikolic | 6-3,6-4 |
| ITF Macedonia F1 Qual | 2016/06/20 08:00 | Petar Conkic v Gabriel Donev | 6-3,6-4 |
| ITF Bulgaria F1 | 2016/05/21 08:00 | Gabriel Donev v Alexander Lazov | 0-6,4-6 |
| ITF Serbia F2 | 2016/07/31 08:00 | Kristijan Mesaros v Ljubomir Celebic | 6-3,3-6,6-3 |
| ITF Serbia F2 | 2016/07/30 09:45 | Ljubomir Celebic v Pawel Juszczak | 3-6,6-1,6-2 |
| ITF Serbia F2 | 2016/07/29 09:00 | Dejan Katic v Ljubomir Celebic | 2-6,4-6 |
| ITF Serbia F2 | 2016/07/28 08:00 | Nicholas Horton v Ljubomir Celebic | 4-6,3-6 |
| ITF Italy F20 | 2016/07/14 15:25 | Ljubomir Celebic v Daniele Capecchi | 2-6,3-6 |
| ITF Italy F20 | 2016/07/12 10:00 | Ljubomir Celebic v Enrico Dalla Valle | 6-4,6-3 |
| ITF Macedonia F1 | 2016/07/08 10:05 | Kristijan Mesaros v Ljubomir Celebic | 6-3,6-1 |
| ITF Macedonia F1 | 2016/07/07 10:30 | Igor Saveljic v Ljubomir Celebic | 2-6,0-6 |