Round: 44 Ground: Clay
| ITF Macedonia F1 Qual | 2016/06/20 08:00 | Conkic, Petar v Gabriel Donev | 6-3,6-4 |
| ITF Bulgaria F1 | 2016/05/21 08:00 | Gabriel Donev v Lazov, Alexander | 0-6,4-6 |
| ITF Bulgaria F1 | 2016/05/20 09:25 | Ouvrard, Victor v Gabriel Donev | 4-6,2-6 |
| ITF Bulgaria F1 | 2016/05/19 09:15 | Gabriel Donev v Frigerio, Lorenzo | 3-6,7-5,6-2 |
| ITF Bulgaria F1 | 2016/05/18 07:30 | Gabriel Donev v Micov, Stefan | 4-6,6-0,7-5 |
| ITF Bulgaria F1 | 2015/06/09 09:00 | Esteve Lobato, Eduard v Gabriel Donev | 6-1,6-2 |
| ITF Bulgaria F1 Qual | 2015/06/07 07:00 | Gabriel Donev v Atanasov, Martin | 6-2,6-2 |
| ITF Bulgaria F1 Qual | 2015/06/06 11:00 | Gabriel Donev v Skvortsov, Philipp | 6-4,6-3 |
| ITF Macedonia F2 | 2016/06/25 14:00 | Luka Pavlovic v Nikolic, Milos | 0-6,3-6 |
| ITF Macedonia F1 Qual | 2016/06/19 07:00 | Nikolic, Milos v Markovic, Goran | 3-6,2-6 |
| ITF Macedonia F1 Qual | 2016/06/18 08:00 | Nikolic, Milos v Yuichiro Inui | 4-6,6-1,6-2 |
| ITF Greece F5 | 2016/04/17 08:30 | Nikolic, Milos v Addison, Aaron | 6-7,4-6 |
| ITF Greece F5 | 2016/04/16 06:00 | Nikolic, Milos v Mudge, Robbie | 6-4,6-3 |
| ITF Greece F4 | 2016/04/10 10:00 | Urbanija, Mike v Nikolic, Milos | 6-1,6-1 |
| ITF Greece F9 Qual | 2015/10/24 11:00 | Nikolic, Milos v Sergi Perez Contri | 3-6,4-6 |
| ITF Greece F8 | 2015/10/21 10:25 | Bjelica, Ivan v Nikolic, Milos | 6-2,7-6 |