| UTR Pro Florida | 2023/05/22 16:30 | Jackson Caldwell v Adit Sinha | 3-6,2-6 |
| UTR Pro Florida | 2023/04/02 18:45 | Jose Garcia v Jackson Caldwell | 6-3,1-1 |
| UTR Pro Florida | 2023/04/01 18:30 | Jackson Caldwell v Felipe Pinzon Moreno | 6-3,6-2 |
| UTR Pro Florida | 2023/03/30 19:30 | Evan Wen v Jackson Caldwell | 6-3,6-7,4-6 |
| UTR Pro Florida | 2023/03/29 16:30 | Perez, Alfredo v Jackson Caldwell | 7-5,6-4 |
| UTR Pro Florida | 2023/03/27 16:00 | Nicholas Heng v Jackson Caldwell | 3-6,6-3,6-2 |
| UTR Pro Florida | 2023/02/04 20:01 | Joseph Chen v Jackson Caldwell | 2-6,1-5 |
| UTR Pro Florida | 2023/02/03 20:15 | Mikel Anderson v Jackson Caldwell | 2-6,4-6 |
| UTR Pro Florida | 2023/05/22 18:04 | Nortey, Isaac Nortie v Leonardo Dal Boni | 6-4,6-2 |
| UTR Pro Florida | 2023/05/13 15:00 | Dmitry Popko v Nortey, Isaac Nortie | 6-1,6-0 |
| UTR Pro Florida | 2023/05/11 19:30 | Nortey, Isaac Nortie v Nettles, Jibril | 6-7,6-1,6-1 |
| UTR Pro Florida | 2023/05/10 18:30 | Nortey, Isaac Nortie v Michael Zhu | 6-2,5-2 |
| UTR Pro Florida | 2023/05/09 18:00 | Nortey, Isaac Nortie v Colas Sanchez, Alberto | 2-6,4-6 |
| UTR Pro Florida | 2023/05/08 19:30 | Nortey, Isaac Nortie v Chad Kissell | 6-4,5-4 |
| UTR Pro Florida | 2023/05/06 15:00 | Acevedo, Nicolas v Nortey, Isaac Nortie | 6-2,5-3 |
| UTR Pro Florida | 2023/05/05 19:30 | Lachlan Brain v Nortey, Isaac Nortie | 5-7,1-6 |