Round: 60 Ground: Clay
| 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 Germany F4 | 2016/06/19 09:00 | Jonas Maier v Vasil Kirkov | 3-6,4-6 |
| ITF Netherlands F1 Qual | 2016/06/12 08:00 | Vasil Kirkov v Fabian Fallert | 6-4,2-6,2-6 |