Round: 44 Ground: Hardcourt outdoor
| Waco, Singles M-ITF-USA-41A | 2019/10/13 17:30 | Alastair Gray v Eliot Spizzirri | 6-7,6-3,12-10 |
| Chiswick, Singles W-ITF-GBR-09A | 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 Petit, Gabriel | 6-2,6-1 |
| ITF M25 Roehampton | 2019/07/31 13:55 | Roumane, Rayane 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 Bauvy, Romain | 7-5,6-0 |
| ITF M25 Roehampton | 2019/07/29 13:40 | Michael Shaw v Alastair Gray | 1-6,2-6 |
| Waco, Singles M-ITF-USA-41A | 2019/10/13 17:30 | Maginley, J. v Kirkov, Vasil | 1-6,6-4,8-10 |
| ITF M15 Cancun | 2019/08/27 14:10 | Kirkov, Vasil v Rousseau, Hillel | 6-3,6-4 |
| Challenger Lexington | 2019/07/31 17:50 | Kirkov, Vasil v Akira Santillan | 4-6,3-6 |
| Challenger Lexington | 2019/07/30 14:30 | Shane, Ryan v Kirkov, Vasil | 3-6,6-1,3-6 |
| Rochester, Singles M-ITF-USA-19A | 2019/06/26 23:05 | Strong Kirchheimer v Kirkov, Vasil | 6-4,6-1 |
| Orlando, Singles Qualifying M-ITF-USA-17A | 2019/06/21 14:00 | Kirkov, Vasil v Hidalgo, Diego | 1-6,4-6 |
| Orlando, Singles Qualifying M-ITF-USA-17A | 2019/06/20 13:00 | Keenan Mayo v Kirkov, Vasil | 3-6,3-6 |
| Orlando, Singles Qualifying M-ITF-USA-17A | 2019/06/18 14:00 | Ravichander, Ishaan v Kirkov, Vasil | 2-6,0-6 |