Round: 28 Ground: Clay
| ITF Turkey F20 | 2016/05/20 10:00 | Dimitar Kuzmanov v Simeon Rossier | 3-6,6-1,6-0 |
| ITF Turkey F20 | 2016/05/19 09:35 | Dimitar Kuzmanov v Seungri Choi | 6-1,6-4 |
| ITF Turkey F20 | 2016/05/17 09:50 | Dimitar Kuzmanov v Mitchell Thomas McDaniels | 6-2,6-1 |
| Challenger Barletta | 2016/04/12 11:00 | Lorenzo Sonego v Dimitar Kuzmanov | 6-4,2-6,6-2 |
| Challenger Napoli | 2016/04/05 10:15 | Marius Copil v Dimitar Kuzmanov | 6-3,4-6,6-2 |
| Challenger Napoli | 2016/04/03 13:55 | Marco Bortolotti v Dimitar Kuzmanov | 3-6,7-5,6-7 |
| Challenger Napoli | 2016/04/02 13:50 | Lorenzo Sonego v Dimitar Kuzmanov | 5-7,2-6 |
| Davis Cup | 2016/03/06 10:00 | Marsel Ilhan v Dimitar Kuzmanov | 4-6,6-2,6-4,4-6,6-0 |
| ITF Turkey F20 | 2016/05/20 08:00 | Nils Brinkmann v Filipp Kekercheni | 2-6,0-6 |
| ITF Turkey F20 | 2016/05/19 09:40 | Filipp Kekercheni v Christoph Negritu | 6-3,6-1 |
| ITF Turkey F20 | 2016/05/17 11:00 | Filipp Kekercheni v Isa Mammetgulyyev | 6-3,6-1 |
| ITF Turkey F19 | 2016/05/11 09:25 | Florent Diep v Filipp Kekercheni | 6-2,2-6,6-3 |
| ITF Tunisia F16 | 2016/04/29 11:10 | Filipp Kekercheni v Omar Salman | 3-6,6-3,3-6 |
| ITF Tunisia F16 | 2016/04/28 09:00 | Pol Toledo Bague v Filipp Kekercheni | 5-7,6-4,3-6 |
| ITF Tunisia F16 | 2016/04/26 12:15 | Filipp Kekercheni v Bruno L F Ureta | 6-2,6-3 |
| ITF Tunisia F15 | 2016/04/18 08:30 | Filipp Kekercheni v Vitalii Shcherba | 6-1,6-3 |