Round: 62 Ground: Clay
| ITF Mexico F4 | 2015/05/18 17:55 | Jarryd Chaplin v Milen Ianakiev | 6-1,3-6,6-2 |
| ITF Mexico F4 | 2015/05/17 16:00 | Ivar Jose Aramburu Contreras v Milen Ianakiev | 7-6,3-6,4-6 |
| ITF Mexico F4 | 2015/05/16 17:00 | Jose Antonio Rodriguez Rodriguez v Milen Ianakiev | 6-3,6-7,4-6 |
| ITF USA F26 Qual | 2014/09/19 09:00 | Brian Battistone v Milen Ianakiev | 6-3,6-4 |
| ITF USA F24 Qual | 2014/09/05 19:00 | Milen Ianakiev v Reilly Opelka | 4-6,4-6 |
| ITF Latvia F1 | 2014/08/03 07:00 | Milen Ianakiev v Brandon Walkin | 6-2,3-6,1-6 |
| ITF Mexico F5 | 2014/05/20 18:50 | Milen Ianakiev v Pavel Krainik | 2-6,2-6 |