Stadium: Court 1 Round: 54 Ground: Hardcourt outdoor
| 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 Doha | 2019/03/07 15:10 | Adrian Obert v Milen Ianakiev | 4-6,2-6 |
| ITF - M15 Heraklion | 2019/05/07 07:00 | Stamatios Kapiris v Jack Gibbens | 6-4,7-5 |
| ITF M15 Las Palmas | 2019/04/29 14:00 | Jack Gibbens v Alessandro Coppini | 6-4,1-6,2-10 |
| ITF - M25 - Sunderland | 2019/04/08 08:00 | Jack Gibbens v Scott Duncan | 3-6,5-7 |
| ITF - M15 - Antalya | 2019/02/04 07:00 | Sho Shimabukuro v Jack Gibbens | 6-0,6-0 |
| ITF - M15 Manacor | 2019/01/07 09:00 | Dennis Uspensky v Jack Gibbens | 6-4,6-4 |
| ITF Greece F8 | 2018/11/11 08:00 | Martin Dimitrov v Jack Gibbens | 6-3,6-4 |
| ITF Greece F8 | 2018/11/10 07:30 | Jack Gibbens v Kenta Kurita | 3-6,6-1,7-6 |
| ITF Greece F7 | 2018/11/07 07:30 | Michail Pervolarakis v Jack Gibbens | 6-4,6-1 |