Round: 25 Ground: Clay
| ITF USA F37 | 2016/11/13 17:00 | Vasil Kirkov v Jack Mingjie Lin | 4-6,0-6 |
| ITF USA F36 | 2016/11/08 15:30 | Vasil Kirkov v Wil Spencer | 1-6,3-6 |
| US Open Qual | 2016/08/23 15:00 | Vasil Kirkov v Yannik Reuter | 2-6,5-7 |
| ITF USA F25 | 2016/07/27 14:00 | Vasil Kirkov v Evan King | 4-6,2-6 |
| ITF USA F25 Qual | 2016/07/25 15:00 | Vasil Kirkov v Sameer Kumar | 6-4,6-4 |
| ITF USA F25 Qual | 2016/07/23 13:30 | Vasil Kirkov v Alafia Ayeni | 6-2,6-4 |
| ITF USA F24 | 2016/07/19 14:00 | Vasil Kirkov v Christian Harrison | 2-6,3-6 |
| ITF Germany F4 | 2016/06/20 11:00 | Jakob Sude v Vasil Kirkov | 7-6,6-3 |
| ITF Czech Republic F12 | 2016/12/08 10:50 | Sami Reinwein v Robin Stanek | 4-6,4-6 |
| ITF Czech Republic F12 | 2016/12/07 09:00 | Jan Mertl v Sami Reinwein | 6-7,6-3,6-7 |
| ITF Czech Republic F12 | 2016/12/06 09:00 | Sami Reinwein v Filip Brtnicky | 6-3,3-6,6-3 |
| ITF Czech Republic F11 | 2016/11/29 10:50 | Matej Maruscak v Sami Reinwein | 6-4,6-4 |
| ITF Norway F3 | 2016/11/03 13:10 | Sami Reinwein v Dragos Nicolae Madaras | 3-6,1-6 |
| ITF Norway F3 | 2016/11/02 10:30 | Sami Reinwein v Jonathan Mridha | 6-4,6-2 |
| ITF Norway F3 | 2016/11/01 10:00 | Sami Reinwein v Alen Avidzba | 7-5,7-6 |
| ITF Norway F2 | 2016/10/26 08:00 | Hugo Grenier v Sami Reinwein | 4-6,6-3,6-2 |