Round: 27 Ground: Clay
| 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 |
| Davis Cup | 2016/03/04 10:00 | Cem Ilkel v Dimitar Kuzmanov | 7-6,1-6,6-4,1-6,7-5 |
| ITF Turkey F20 | 2016/05/19 08:00 | Ewen Lumsden v Simeon Rossier | 3-6,1-6 |
| ITF Turkey F19 | 2016/05/11 09:25 | Anil Yuksel v Simeon Rossier | 6-4,6-2 |
| ITF Nigeria F2 MD | 2016/04/26 15:05 | Simeon Rossier v David Pel | 2-6,3-6 |
| ITF Turkey F14 | 2016/04/07 08:40 | Elmar Ejupovic v Simeon Rossier | 6-3,6-0 |
| ITF Turkey F14 | 2016/04/05 09:30 | Simeon Rossier v David Perez Sanz | 6-4,3-6,6-4 |
| ITF Italy F2 Qual | 2016/03/06 13:00 | Simeon Rossier v Andrew Ruppli | 3-6,4-6 |
| ITF Italy F2 Qual | 2016/03/05 12:30 | Simeon Rossier v Nicolo Turchetti | 7-6,6-7,7-5 |
| ITF Italy F1 Qual | 2016/02/28 08:30 | Simeon Rossier v Fran Zvonimir Zgombic | 6-7,6-4,4-6 |