Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Doha | 2020/03/10 12:00 | Milen Ianakiev v Mohammed Abdulla | 6-2,6-2 |
| ITF M15 Heraklion | 2019/12/08 10:00 | Milen Ianakiev v Sizya Ernest Kivanda | 2-6,6-2,8-10 |
| ITF M15 Heraklion | 2019/12/02 09:30 | Gianmarco Amatiste v Milen Ianakiev | 3-6,6-3,10-4 |
| ITF M15 Heraklion | 2019/12/01 14:00 | Frane Nincevic v Milen Ianakiev | 3-6,6-4,8-10 |
| 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 |
| ATP Doha | 2020/01/04 09:10 | Rashed Nawaf v Thiago Monteiro | 2-6,0-6 |
| ITF M15 Doha | 2019/10/23 16:15 | Tobias Simon v Rashed Nawaf | 6-3,6-0 |