Round: 44 Ground: Hardcourt outdoor
| ITF M25 Waco | 2019/10/13 17:30 | Alastair Gray v Eliot Spizzirri | 6-7,6-3,12-10 |
| ITF M25 Chiswick | 2019/08/06 11:15 | Alastair Gray v Charles Broom | 4-6,6-2,3-6 |
| ITF M25 - Roehampton | 2019/08/02 10:00 | Daniel Cukierman v Alastair Gray | 6-2,4-6,6-4 |
| ITF M25 - Roehampton | 2019/08/01 09:30 | Alastair Gray v Gabriel Petit | 6-2,6-1 |
| ITF M25 - Roehampton | 2019/07/31 13:55 | Rayane Roumane v Alastair Gray | 1-6,4-6 |
| ITF M25 - Roehampton | 2019/07/31 08:30 | Alastair Gray v Filip Duda | 6-2,6-3 |
| ITF M25 - Roehampton | 2019/07/29 16:30 | Alastair Gray v Romain Bauvy | 7-5,6-0 |
| ITF M25 - Roehampton | 2019/07/29 13:40 | Michael Shaw v Alastair Gray | 1-6,2-6 |
| ITF M25 Waco | 2019/10/13 17:30 | Herbert Jody Maginley v Vasil Kirkov | 1-6,6-4,8-10 |
| ITF M15 - Cancun | 2019/08/27 14:10 | Vasil Kirkov v Hillel Rousseau | 6-3,6-4 |
| Challenger - Lexington | 2019/07/31 17:50 | Vasil Kirkov v Akira Santillan | 4-6,3-6 |
| Challenger - Lexington | 2019/07/30 14:30 | Ryan Shane v Vasil Kirkov | 3-6,6-1,3-6 |
| ITF M15 - Rochester | 2019/06/26 23:05 | Strong Kirchheimer v Vasil Kirkov | 6-4,6-1 |
| ITF M15 Orlando | 2019/06/21 14:00 | Vasil Kirkov v Diego Hidalgo | 1-6,4-6 |
| ITF M15 Orlando | 2019/06/20 13:00 | Keenan Mayo v Vasil Kirkov | 3-6,3-6 |
| ITF M15 Orlando | 2019/06/18 14:00 | Ishaan Ravichander v Vasil Kirkov | 2-6,0-6 |