Round: 44 Ground: Hardcourt outdoor
| 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 |
| ITF USA F15 | 2016/04/30 19:00 | Martins Podzus v Vasil Kirkov | 6-2,6-3 |
| Challenger Tampere | 2016/07/19 07:00 | Ruben R. Hidalgo v Yannik Reuter | 7-6,7-6 |
| Challenger Marburg | 2016/07/01 16:00 | Yannik Reuter v Marco Trungelliti | 7-5,3-6,3-6 |
| Challenger Marburg | 2016/06/30 11:45 | Andrea Arnaboldi v Yannik Reuter | 6-7,1-6 |
| Challenger Marburg | 2016/06/29 16:00 | Yannik Reuter v Gerald Melzer | 3-6,6-1,6-4 |
| Challenger Marburg | 2016/06/28 16:40 | Julian Lenz v Yannik Reuter | 4-6,3-6 |
| Challenger Marburg Qual | 2016/06/27 12:55 | Yannik Reuter v Edoardo Eremin | 3-6,7-6,7-5 |
| Challenger Marburg Qual | 2016/06/26 09:15 | Yannik Reuter v Mats Moraing | 7-6,6-7,6-3 |
| Challenger Milan Qual | 2016/06/22 15:25 | Carlos Berlocq v Yannik Reuter | 6-4,6-0 |