Stadium: Hard Court 13 Round: 25 Ground: Hardcourt outdoor
| ITF - M15 Héraklion | 2019/05/20 07:00 | Omni Kumar v Boyer, Toby D | 3-6,7-6,4-10 |
| ITF - M15 Héraklion | 2019/05/15 07:00 | Addison, Aaron v Omni Kumar | 4-6,7-6,6-2 |
| ITF - M15 Héraklion | 2019/05/14 07:00 | Omni Kumar v Jhun, Alexander | 5-7,6-4,10-8 |
| ITF - M15 Héraklion | 2019/05/09 09:55 | Boyer, Dusty H v Omni Kumar | 6-3,6-4 |
| ITF - M15 Héraklion | 2019/05/08 09:20 | Omni Kumar v Hoeveler, Leon | 6-1,6-1 |
| ITF M15 Cancun | 2019/03/11 20:00 | Omni Kumar v Newman, Baker | 4-6,4-6 |
| ITF M15 Cancun | 2019/03/11 15:30 | Omni Kumar v Gostincar, Domen | 6-4,6-4 |
| Tucson, Singles M-ITF-USA-07A | 2019/02/12 16:30 | Omni Kumar v George Goldhoff | 4-6,0-6 |
| 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 |
| ITF M15 Sozopol | 2019/05/09 07:00 | Lozan, Kristian v Ianakiev, Milen | 6-2,6-4 |
| ITF M15 Sozopol | 2019/05/08 07:00 | Ianakiev, Milen v Gueydan, Quentin | 6-4,6-3 |