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