| Davis Cup | 2021/07/01 15:35 | Jesse Flores v Alejandro Obando | 6-4,4-6,6-0 |
| Davis Cup | 2021/06/30 16:30 | Jesse Flores v Nkrumah Patrick | 6-1,6-1 |
| ITF M25 Santo Domingo | 2021/06/09 13:00 | Calvin Hemery v Jesse Flores | 7-6,7-6 |
| ITF M25 Santo Domingo | 2021/06/01 12:50 | Luis Patino v Jesse Flores | 7-5,6-3 |
| ITF M25 Santo Domingo | 2021/05/31 15:30 | Jasel Beltre v Jesse Flores | 3-6,1-6 |
| ITF M25 Santo Domingo | 2021/05/30 15:30 | Mateo Barreiros Reyes v Jesse Flores | 2-6,4-6 |
| ITF M25 Pensacola | 2021/05/18 16:10 | John Bernard v Jesse Flores | 6-3,1-6,11-9 |
| ITF M25 Pensacola | 2021/05/17 15:30 | Jack Vance v Jesse Flores | 2-6,4-6 |
| Davis Cup | 2021/07/01 15:35 | Tariq Simons v Nkrumah Patrick | 6-0,6-0 |
| Davis Cup | 2021/06/30 16:00 | Alejandro Obando v Tariq Simons | 6-1,6-3 |
| Davis Cup | 2019/06/21 16:25 | Osmel Rivera Granja v Tariq Simons | 6-1,6-3 |
| Davis Cup | 2019/06/19 18:00 | Rowland Phillips v Tariq Simons | 6-2,6-2 |