Stadium: Hard Court 5 Round: 27 Ground: Hardcourt outdoor
| ITF - M15 Heraklion | 2019/05/22 09:30 | Pablo Vivero Gonzalez v Gabriel Donev | 4-6,4-6 |
| ITF - M15 Heraklion | 2019/05/20 11:00 | Gabriel Donev v Moritz Thiem | 0-6,6-3,10-7 |
| ITF - M15 Heraklion | 2019/05/20 07:00 | Gabriel Donev v Vasilios Caripi | 6-1,6-0 |
| ITF - M15 Heraklion | 2019/05/16 10:05 | Marek Jaloviec v Gabriel Donev | 6-3,6-2 |
| ITF - M15 Heraklion | 2019/05/15 11:55 | Brandon Murphy v Gabriel Donev | 3-6,3-6 |
| ITF M15 - Sozopol | 2019/05/08 08:00 | Gabriel Donev v Boris Pokotilov | 5-7,6-4,6-4 |
| ITF M15 - Sunrise | 2019/04/08 15:00 | Alexander Knight v Gabriel Donev | 6-4,6-3 |
| ITF M15 - Cancun | 2019/03/27 16:30 | Gabriel Donev v Andrew Watson | 0-6,2-6 |
| ITF - M15 Heraklion | 2019/05/23 11:00 | Jonas Trinker v Patrik Nema | 6-4,6-2 |
| ITF - M15 Heraklion | 2019/05/22 11:40 | Aaron Addison v Jonas Trinker | 2-6,6-7 |
| ITF - M15 Heraklion | 2019/05/20 11:00 | Jonas Trinker v Loic Ratsaratany | 6-4,6-4 |
| ITF - M15 Heraklion | 2019/05/20 07:00 | Jonas Trinker v Elliott Farmer | 6-4,6-1 |
| ITF - M15 Heraklion | 2019/05/16 09:55 | Jonas Trinker v Edan Leshem | 3-6,4-6 |
| ITF - M15 Heraklion | 2019/05/15 07:00 | Jonas Trinker v Moritz Thiem | 6-4,6-1 |
| ITF - M15 Heraklion | 2019/05/11 07:30 | Jonas Trinker v Michail Pervolarakis | 3-6,4-6 |
| ITF - M15 Heraklion | 2019/05/10 07:00 | Lloyd Glasspool v Jonas Trinker | 4-6,4-6 |