Stadium: Hard 4 Round: 44 Ground: Hardcourt outdoor
| ITF M25 Chiswick | 2019/08/05 14:10 | Milen Ianakiev v Sizya Ernest Kivanda | 2-6,4-6 |
| 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 |
| 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 Milovice | 2019/11/11 11:00 | Sizya Ernest Kivanda v Samuel Puskar | 3-6,6-7 |
| ITF - M25 Falun | 2019/09/29 11:00 | Carl Gustafsson v Sizya Ernest Kivanda | 6-7,6-4,10-7 |
| ITF - M25 Shrewsbury | 2019/09/24 13:50 | Anton Matusevich v Sizya Ernest Kivanda | 6-4,6-4 |
| ITF - M25 Shrewsbury | 2019/09/23 14:20 | Sizya Ernest Kivanda v Jack Oswald | 7-5,6-2 |
| ITF - M25 Shrewsbury | 2019/09/23 10:10 | Sizya Ernest Kivanda v Tom Skinner | 7-6,7-6 |
| ITF M15 Pajulahti | 2019/09/18 09:25 | Francesco Vilardo v Sizya Ernest Kivanda | 6-3,6-3 |
| ITF M15 Pajulahti | 2019/09/17 07:30 | Sizya Ernest Kivanda v Alexander Chepik | 6-3,7-6 |
| ITF - M25 Mulhouse | 2019/09/08 13:30 | Sizya Ernest Kivanda v Yannik Steinegger | 5-7,6-2,7-10 |