Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| ITF M25 Malibu | 2019/11/05 21:10 | Drew Baird v Milen Ianakiev | 6-3,6-3 |
| ITF M25 Malibu | 2019/11/04 18:00 | Chris Wettengel v Milen Ianakiev | 6-2,3-6,3-10 |
| ITF M25 Claremont | 2019/10/07 18:00 | Milen Ianakiev v Diego Nava | 6-4,3-6,8-10 |
| ITF M25 Chiswick | 2019/08/05 14:10 | Milen Ianakiev v Sizya Ernest Kivanda | 2-6,4-6 |
| ITF M25 Roehampton | 2019/07/29 08:30 | Milen Ianakiev v Sacha Modica | 4-6,2-6 |
| ITF M15 Plovdiv | 2019/06/04 06:30 | Milen Ianakiev v Andrea Bessire | 4-6,2-6 |
| ITF M15 Plovdiv | 2019/06/03 10:00 | Milen Ianakiev v Cosmin Ontica | 1-6,6-4,10-6 |
| ITF M15 Heraklion | 2019/05/28 09:00 | Omni Kumar v Milen Ianakiev | 6-3,7-5 |
| ITF M15 Doha | 2019/10/23 16:15 | Tobias Simon v Rashed Nawaf | 6-3,6-0 |