Stadium: Central Hard Court Round: 25 Ground: Hardcourt outdoor
| ITF M25 Fayetteville | 2019/10/23 20:15 | Jacob Dunbar v Vasil Kirkov | 3-6,6-2,6-1 |
| ITF M25 Waco | 2019/10/16 20:10 | Vasil Kirkov v Ben Patael | 4-6,1-6 |
| ITF M25 Waco | 2019/10/15 19:25 | Eric Morris v Vasil Kirkov | 0-6,1-6 |
| ITF M25 Waco | 2019/10/14 17:00 | Alastair Gray v Vasil Kirkov | 4-6,4-6 |
| 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 Heraklion | 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 Adam Nagoudi | 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 | Maksim Tikhomirov 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 Philip Bachmaier | 7-6,6-7,8-10 |
| ITF M15 Antalya | 2019/10/07 07:00 | Petros Tsitsipas v Bekir Berk Sahin | 7-6,6-0 |