Round: 60 Ground: Hardcourt outdoor
| ITF USA F28 | 2016/09/11 16:30 | Alexei Popyrin v Patrick Kawka | 6-3,7-5 |
| ITF USA F28 | 2016/09/10 16:00 | Emilio Nava v Patrick Kawka | 1-6,1-6 |
| ITF USA F28 | 2016/09/09 23:00 | Alexander Cozbinov v Milen Ianakiev | 6-2,6-3 |
| ITF Germany F10 Qual | 2016/08/07 13:00 | Milen Ianakiev v Joel Vincent Link | 4-6,1-6 |
| ITF Egypt F15 | 2016/07/10 16:00 | Milen Ianakiev v Alan Gadjiev | 3-6,6-3,3-6 |
| ITF Egypt F15 | 2016/07/09 14:00 | Milen Ianakiev v Mohit Jain | 6-3,6-2 |
| ITF Egypt F14 | 2016/07/04 17:45 | Milen Ianakiev v Ksawery Pociej | 2-6,2-6 |
| ITF Egypt F14 | 2016/07/03 18:00 | Milen Ianakiev v Mohit Jain | 6-1,6-1 |
| ITF Egypt F13 | 2016/06/29 19:30 | Milen Ianakiev v Javier Pulgar-Garcia | 3-6,2-6 |
| ITF Egypt F13 | 2016/06/27 17:45 | Milen Ianakiev v Hugo Largo | 7-5,6-1 |