Stadium: Cancha 4 Round: 14 Ground: Hardcourt outdoor
| ITF M25 Santo Domingo | 2023/02/16 13:30 | Daniel Dutra Da Silva v Jesse Flores | 2-6,7-6,6-2 |
| ITF M25 Santo Domingo | 2023/02/15 16:55 | Preston Brown v Jesse Flores | 2-6,2-6 |
| UTR Pro Pozos | 2023/01/16 22:00 | Meethre Barot v Jesse Flores | 1-6,1-6 |
| UTR Pro Pozos | 2023/01/14 18:00 | Ignacio Buse v Jesse Flores | 6-4,6-5 |
| UTR Pro Pozos | 2023/01/13 22:00 | Anthony Wright v Jesse Flores | 6-4,2-6,3-5 |
| UTR Pro Pozos | 2023/01/12 23:08 | Daniel Salazar v Jesse Flores | 3-6,6-7 |
| UTR Pro Pozos | 2023/01/10 21:59 | Christian Heaney-Secord v Jesse Flores | 2-6,2-5 |
| UTR Pro Pozos | 2023/01/09 17:30 | Jesse Flores v Alejandro Mendoza | 6-2,6-1 |
| ITF M15 Weston | 2023/02/17 16:00 | Kristjan Tamm v Federico Agustin Gomez | 2-6,5-7 |
| ITF M15 Weston | 2023/02/16 16:50 | Kristjan Tamm v Juan David Velasquez | 7-5,6-3 |
| ITF M15 Weston | 2023/02/15 19:25 | Sekou Bangoura v Kristjan Tamm | 4-6,3-6 |
| ITF M15 Palm Coast | 2023/02/07 16:30 | Rei Sakamoto v Kristjan Tamm | 7-6,2-6,6-3 |
| Davis Cup | 2023/02/05 19:15 | Blaise Bicknell v Kristjan Tamm | 7-6,0-0 |
| Davis Cup | 2023/02/04 20:30 | Rowland Phillips v Kristjan Tamm | 6-1,6-1 |
| ITF M25 Al Zahra | 2023/01/26 07:00 | Kristjan Tamm v Sidane Pontjodikromo | 4-6,3-6 |
| ITF M25 Al Zahra | 2023/01/25 08:55 | Kristjan Tamm v Maxim Zhukov | 6-3,3-6,6-4 |