Stadium: Central Hard Court Round: 25 Ground: Hardcourt outdoor
| Fayetteville, AR, Singles Qualifying, M-ITF-USA-31 | 2019/10/23 20:15 | Dunbar, Jacob v Kirkov, Vasil | 3-6,6-2,6-1 |
| Waco, Singles M-ITF-USA-41A | 2019/10/16 20:10 | Kirkov, Vasil v Patael, Ben | 4-6,1-6 |
| Waco, Singles M-ITF-USA-41A | 2019/10/15 19:25 | Morris, Eric v Kirkov, Vasil | 0-6,1-6 |
| Waco, Singles M-ITF-USA-41A | 2019/10/14 17:00 | Alastair Gray v Kirkov, Vasil | 4-6,4-6 |
| 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 |
| ITF - M15 Héraklion | 2019/11/06 12:55 | Lucas Catarina v Petros Tsitsipas | 6-2,6-4 |
| ITF M25 Monastir | 2019/10/28 11:00 | Alafia Ayeni v Petros Tsitsipas | 6-3,6-1 |
| ITF M25 Monastir | 2019/10/27 14:00 | Petros Tsitsipas v Nagoudi, Adam | 6-4,6-4 |
| ITF M25 Monastir | 2019/10/27 10:30 | Buvaysar Gadamauri v Petros Tsitsipas | 3-6,4-6 |
| ITF M25 Monastir | 2019/10/22 09:00 | Tikhomirov, Maksim v Petros Tsitsipas | 6-2,1-6,6-1 |
| ITF M25 Monastir | 2019/10/21 09:00 | Petros Tsitsipas v Buvaysar Gadamauri | 6-4,6-3 |
| ITF - M15 Antalya | 2019/10/08 07:00 | Petros Tsitsipas v Bachmaier, Philip | 7-6,6-7,8-10 |
| ITF - M15 Antalya | 2019/10/07 07:00 | Petros Tsitsipas v Bekir Berk Sahin | 7-6,6-0 |