Stadium: Court 2 Round: 54 Ground: Hardcourt outdoor
| ITF M15 Heraklion | 2019/05/13 07:00 | Milen Ianakiev v Jack Gibbens | 6-2,6-7,10-8 |
| ITF M15 Sozopol | 2019/05/09 07:00 | Kristian Lozan v Milen Ianakiev | 6-2,6-4 |
| ITF M15 Sozopol | 2019/05/08 07:00 | Milen Ianakiev v Quentin Gueydan | 6-4,6-3 |
| ITF M15 Tel Aviv | 2019/03/27 08:00 | Milen Ianakiev v Martin Van Der Meerschen | 3-6,6-4,4-6 |
| ITF M15 Tel Aviv | 2019/03/26 11:30 | Milen Ianakiev v Joshua Luck | 6-3,6-1 |
| ITF M15 Tel Aviv | 2019/03/26 07:30 | Milen Ianakiev v Sahar Simon | 6-2,6-3 |
| ITF M15 Manama | 2019/03/19 10:15 | Vitaliy Sachko v Milen Ianakiev | 4-6,7-5,6-3 |
| ITF M15 Doha | 2019/03/08 13:00 | Milen Ianakiev v Geoffrey Blancaneaux | 1-6,2-6 |
| ITF M15 Heraklion | 2019/05/13 07:00 | Vasilios Caripi v Jesse Delaney | 7-6,3-6,5-10 |
| ITF M15 Heraklion | 2019/05/07 10:00 | Lloyd Glasspool v Jesse Delaney | 6-4,6-0 |
| ITF M15 Mornington | 2019/03/27 02:25 | Jesse Delaney v Brandon Walkin | 3-6,4-6 |
| ITF M15 Mornington | 2019/03/25 23:00 | Jesse Delaney v Masayoshi Ono | 6-2,3-6,10-8 |
| ITF M15 Mornington | 2019/03/24 23:00 | Matthew Dellavedova v Jesse Delaney | 6-7,5-7 |
| ITF M15 Mornington | 2019/03/17 23:00 | Jesse Delaney v Matyas Fuele | 6-7,3-6 |
| ITF Vietnam F5 | 2018/10/28 03:00 | George Botezan v Jesse Delaney | 7-6,6-4 |
| ITF Vietnam F4 | 2018/10/22 02:30 | Nitin Kumar Sinha v Jesse Delaney | 7-6,6-3 |