Stadium: Hard 4 Round: 44 Ground: Hardcourt outdoor
| Chiswick, Singles W-ITF-GBR-09A | 2019/08/05 14:10 | Ianakiev, Milen v Sizya Ernest Kivanda | 2-6,4-6 |
| 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 |
| ITF M25 Roehampton | 2019/07/29 08:30 | Ianakiev, Milen v Modica, Sacha | 4-6,2-6 |
| Plovdiv, Singles Qualifying M-ITF-BUL-03A | 2019/06/04 06:30 | Ianakiev, Milen v Bessire, Andrea | 4-6,2-6 |
| Milovice, Singles M-ITF-CZE-10A | 2019/11/11 11:00 | Sizya Ernest Kivanda v Samuel Puskar | 3-6,6-7 |
| ITF M25 Falun | 2019/09/29 11:00 | Gustafsson, Carl 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 Oswald, Jack | 7-5,6-2 |
| ITF M25 Shrewsbury | 2019/09/23 10:10 | Sizya Ernest Kivanda v Skinner, Tom | 7-6,7-6 |
| Pajulahti, Singles M-ITF-FIN-02A | 2019/09/18 09:25 | Vilardo, Francesco v Sizya Ernest Kivanda | 6-3,6-3 |
| Pajulahti, Singles M-ITF-FIN-02A | 2019/09/17 07:30 | Sizya Ernest Kivanda v Alexander Chepik | 6-3,7-6 |
| Mulhouse, Singles M-ITF-FRA-16A | 2019/09/08 13:30 | Sizya Ernest Kivanda v Yannik Steinegger | 5-7,6-2,7-10 |