Round: 62 Ground: Clay
| ITF Bulgaria F1 - Qual. | 2017/05/07 07:00 | Stefan Luckanov v Hristo Valeov | 0-6,1-6 |
| ITF Macedonia F1 - Qual. | 2016/06/19 07:00 | Petar Conkic v Stefan Luckanov | 6-0,6-1 |
| ITF Bulgaria F1 - Qual. | 2015/06/06 07:00 | Ted Bachev v Stefan Luckanov | 6-3,6-3 |
| ITF Turchia F28 | 2017/08/02 07:30 | Muhammet Haylaz v Milen Ianakiev | 6-3,6-7,7-6 |
| ITF Turchia F28 | 2017/07/31 08:00 | Kento Tagashira v Milen Ianakiev | 3-6,6-7 |
| ITF Turchia F27 | 2017/07/24 11:00 | Greg Polmans v Milen Ianakiev | 6-2,2-6,7-6 |
| ITF Turchia F27 | 2017/07/23 07:00 | Milen Ianakiev v Umut Akkoyun | 6-2,6-4 |
| ITF Turchia F27 | 2017/07/22 07:00 | Yusei Fukuoka v Milen Ianakiev | 2-6,1-6 |
| ITF USA F30 | 2016/09/23 20:00 | Milen Ianakiev v Jordan Parker | 4-6,6-4,1-6 |
| ITF USA F29 | 2016/09/17 00:30 | Patrick Kawka v Milen Ianakiev | 6-2,6-3 |
| ITF USA F28 | 2016/09/09 23:00 | Alexander Cozbinov v Milen Ianakiev | 6-2,6-3 |