Stadium: Court04 Round: 25 Ground: Hardcourt outdoor
| Tel Aviv, Singles Qualifying M-ITF-ISR-01A | 2019/03/26 11:30 | Ianakiev, Milen v Joshua Luck | 6-3,6-1 |
| Tel Aviv, Singles Qualifying M-ITF-ISR-01A | 2019/03/26 07:30 | Ianakiev, Milen v Simon, Sahar | 6-2,6-3 |
| Manama, Singles M-ITF-BRN-01A | 2019/03/19 10:15 | Vitaliy Sachko v Ianakiev, Milen | 4-6,7-5,6-3 |
| ITF - M15 Doha | 2019/03/08 13:00 | Ianakiev, Milen v Geoffrey Blancaneaux | 1-6,2-6 |
| ITF - M15 Doha | 2019/03/07 15:10 | Obert, Adrian v Ianakiev, Milen | 4-6,2-6 |
| ITF - M15 Doha | 2019/03/06 19:25 | Dalibor Svrcina v Ianakiev, Milen | 3-6,2-6 |
| ITF - M15 Doha | 2019/03/05 13:50 | Manole, Alexandru Vasile v Ianakiev, Milen | 3-6,5-7 |
| ITF - M15 Doha | 2019/03/04 14:15 | Bencic, Brian v Ianakiev, Milen | 1-6,1-6 |
| ITF - M15 Doha | 2019/03/11 12:00 | Abhinav Sanjeev Shanmugam v van Der Meerschen, Martin | 6-2,3-6,10-3 |
| ITF - M15 Doha | 2019/03/11 08:00 | Richard Zusman v van Der Meerschen, Martin | 5-7,3-6 |
| ITF - M15 Doha | 2019/03/05 12:00 | Sidane Pontjodikromo v van Der Meerschen, Martin | 6-3,6-4 |
| ITF - M15 Doha | 2019/03/04 12:00 | Zarichanskyy, Akim v van Der Meerschen, Martin | 2-6,1-6 |
| ITF - M15 Sharm El Sheikh | 2019/02/18 12:30 | van Der Meerschen, Martin v Khotkov, Oleg | 2-6,5-7 |
| ITF - M15 Sharm El Sheikh | 2019/02/18 07:30 | Ratniuk, Maxim v van Der Meerschen, Martin | 3-6,4-6 |
| ITF M15 Kaarst | 2019/02/06 17:30 | van Der Meerschen, Martin v Lucas Gerch | 2-6,5-7 |
| ITF M15 Kaarst | 2019/02/04 18:20 | van Der Meerschen, Martin v Terczynski, Mateusz | 7-6,2-6,12-10 |