stadio: Court 7 Round: 54 Ground: Clay
| ITF M15 Plovdiv | 2019/06/03 10:00 | Milen Ianakiev v Cosmin Ontica | 1-6,6-4,10-6 |
| ITF M15 Heraklion | 2019/05/28 09:00 | Omni Kumar v Milen Ianakiev | 6-3,7-5 |
| ITF M15 Heraklion | 2019/05/23 08:50 | Andres Artunedo Martinavarr v Milen Ianakiev | 6-3,6-4 |
| ITF M15 Heraklion | 2019/05/22 06:55 | James Story v Milen Ianakiev | 3-6,4-6 |
| ITF M15 Heraklion | 2019/05/20 13:00 | Milen Ianakiev v Alexandros Roumpis | 6-4,6-2 |
| ITF M15 Heraklion | 2019/05/20 07:00 | Milen Ianakiev v George Davies | 6-4,6-3 |
| ITF M15 Heraklion | 2019/05/14 07:00 | Milen Ianakiev v Jesse Delaney | 6-7,6-0,5-10 |
| ITF M15 Heraklion | 2019/05/13 07:00 | Milen Ianakiev v Jack Gibbens | 6-2,6-7,10-8 |
| ITF M15 Plovdiv | 2019/06/03 10:00 | Hristo Valeov v Andrea Bessire | 4-6,5-7 |
| ITF M15 Reggio Emilia | 2019/05/28 11:00 | Andrea Bessire v Davide Albertoni | 2-6,6-3,5-10 |
| ITF M15 Reggio Emilia | 2019/05/27 12:30 | Andrea Bessire v Manuel Massimino | 6-2,6-4 |
| ITF M15 Accra | 2019/05/02 10:55 | Tukhula Jacobs v Andrea Bessire | 7-5,6-1 |
| ITF M15 Accra | 2019/05/01 14:25 | Darryl Hale v Andrea Bessire | 3-6,1-6 |
| ITF M15 Accra | 2019/05/01 12:00 | Darryl Hale v Andrea Bessire | 3-6,1-4 |
| ITF M15 Rovigno | 2019/03/18 09:00 | Moritz Thiem v Andrea Bessire | 6-2,6-4 |
| ITF M15 Porec | 2019/03/11 09:00 | Andrea Bessire v Gabor Borsos | 2-6,6-7 |