Round: 29 Ground: Clay
| ITF Turkey F8 | 2016/02/27 09:00 | Dimitar Kuzmanov v Christopher Heyman | 6-4,6-4 |
| ITF Greece F6 | 2014/04/16 10:30 | Dimitar Kuzmanov v Christopher Heyman | 6-3,6-3 |
| ITF Turkey F20 | 2016/05/21 08:00 | Dimitar Kuzmanov v Filipp Kekercheni | 6-1,6-1 |
| 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 |
| ITF Turkey F20 | 2016/05/21 08:00 | Cem Ilkel v Christopher Heyman | 3-6,6-7 |
| ITF Turkey F20 | 2016/05/20 08:00 | Altug Celikbilek v Christopher Heyman | 2-6,2-6 |
| ITF Turkey F20 | 2016/05/19 08:00 | Muhammet Haylaz v Christopher Heyman | 2-6,1-6 |
| ITF Turkey F20 | 2016/05/18 10:00 | Louroi Martinez v Christopher Heyman | 3-6,1-6 |
| ITF Turkey F17 | 2016/05/01 11:00 | Marc Sieber v Christopher Heyman | 6-3,6-0 |
| ITF Turkey F17 | 2016/04/30 11:00 | Raphael Baltensperger v Christopher Heyman | 1-6,3-6 |
| ITF Turkey F17 | 2016/04/29 11:50 | Miliaan Niesten v Christopher Heyman | 0-6,2-6 |
| ITF Turkey F17 | 2016/04/28 10:55 | Marko Osmakcic v Christopher Heyman | 0-6,0-6 |