Stadium: Costa Rica Country Club Round: 45 Ground: Hardcourt indoor
| Davis Cup | 2020/03/07 01:25 | Jesse Flores v Alexandar Lazarov | 5-7,6-4,3-6 |
| ITF M15 Cancun | 2020/02/20 18:55 | Gage Brymer v Jesse Flores | 6-3,6-4 |
| ITF M15 Cancun | 2020/02/18 16:20 | Jesse Flores v Joshua Ortlip | 6-3,6-3 |
| ITF M15 Cancun | 2020/02/11 15:00 | Jesse Flores v Eduardo Ribeiro | 7-6,4-6,3-10 |
| ITF M15 Cancun | 2020/02/10 15:00 | Jesse Flores v Luis Humberto Lopez | 2-6,2-6 |
| ITF M15 Cancun | 2020/02/09 17:00 | Jesse Flores v Joao Victor Ortega | 6-0,6-0 |
| ITF M15 Cancun | 2020/01/28 15:00 | Alex Hernandez v Jesse Flores | 7-6,3-6,10-7 |
| ITF M15 Cancun | 2020/01/27 14:00 | Luis Humberto Lopez v Jesse Flores | 4-6,2-6 |
| Davis Cup | 2020/03/07 00:00 | Julian Saborio v Dimitar Kuzmanov | 4-6,2-6 |
| ITF M25 Antalya | 2020/02/28 07:30 | Jonas Forejtek v Dimitar Kuzmanov | 6-4,3-6,7-5 |
| ITF M25 Antalya | 2020/02/27 08:25 | Nikolas Sanchez Izquierdo v Dimitar Kuzmanov | 1-6,4-6 |
| ITF M25 Antalya | 2020/02/26 12:25 | Marko Miladinovic v Dimitar Kuzmanov | 6-1,5-7,0-6 |
| Challenger Koblenz | 2020/02/21 12:00 | Dimitar Kuzmanov v Tomas Machac | 4-6,4-6 |
| Challenger Koblenz | 2020/02/20 14:00 | Dimitar Kuzmanov v Dustin Brown | 4-6,6-3,6-4 |
| Challenger Koblenz | 2020/02/19 15:35 | Maxime Janvier v Dimitar Kuzmanov | 4-6,5-7 |
| Challenger Koblenz | 2020/02/17 13:55 | Dimitar Kuzmanov v Vladyslav Orlov | 6-2,6-1 |