Stadium: Hard Court 2 Round: 54 Ground: Hardcourt outdoor
| 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 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 Heraklion | 2019/05/20 07:00 | Alexandros Roumpis v Patrick Foley | 6-4,6-1 |
| ITF M15 Heraklion | 2019/05/08 07:00 | Stamatios Kapiris v Alexandros Roumpis | 7-6,6-0 |
| ITF Greece F8 | 2018/11/13 12:45 | Alexandros Roumpis v Vit Kopriva | 1-6,0-6 |
| ITF Greece F7 | 2018/11/04 08:00 | Alexandros Roumpis v Marvin Rehberg | 4-6,1-6 |
| ITF Greece F7 | 2018/11/03 10:00 | Alexandros Roumpis v Dian Nedev | 6-1,6-2 |
| ITF Lebanon F1 | 2018/09/27 14:45 | Nicolo Turchetti v Alexandros Roumpis | 6-4,6-2 |
| ITF Lebanon F1 | 2018/09/26 15:25 | Kate Fakih v Alexandros Roumpis | 1-6,6-4,3-6 |
| ITF Lebanon F1 | 2018/09/23 13:00 | Stepan Pecak v Alexandros Roumpis | 1-6,2-6 |