Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| ITF - M15 Doha | 2020/03/10 12:00 | Ianakiev, Milen v Abdulla, Mohammed | 6-2,6-2 |
| ITF - M15 Héraklion | 2019/12/08 10:00 | Ianakiev, Milen v Sizya Ernest Kivanda | 2-6,6-2,8-10 |
| ITF - M15 Héraklion | 2019/12/02 09:30 | Amatiste, Gianmarco v Ianakiev, Milen | 3-6,6-3,10-4 |
| ITF - M15 Héraklion | 2019/12/01 14:00 | Nincevic, Frane v Ianakiev, Milen | 3-6,6-4,8-10 |
| ITF M25 Malibu | 2019/11/05 21:10 | Baird, Drew v Ianakiev, Milen | 6-3,6-3 |
| ITF M25 Malibu | 2019/11/04 18:00 | Wettengel, Chris v Ianakiev, Milen | 6-2,3-6,3-10 |
| Claremont, Singles Qualifying M-ITF-USA-06B | 2019/10/07 18:00 | Ianakiev, Milen v Nava, Diego | 6-4,3-6,8-10 |
| Chiswick, Singles W-ITF-GBR-09A | 2019/08/05 14:10 | Ianakiev, Milen v Sizya Ernest Kivanda | 2-6,4-6 |
| ATP - Doha | 2020/01/04 09:10 | Rashed Nawaf v Thiago Monteiro | 2-6,0-6 |
| ITF - M15 Doha | 2019/10/23 16:15 | Simon, Tobias v Rashed Nawaf | 6-3,6-0 |