| 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 | Alfredo Perez 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 | 2023/02/03 15:00 | Isaiah Strode v Jackson Caldwell | 6-3,6-1 |
| UTR Pro Florida | 2023/02/02 18:00 | Christian Oliveira v Jackson Caldwell | 0-0 |
| UTR Pro Florida | 2023/02/01 23:22 | Leonardo Telles v Jackson Caldwell | 4-6,6-1,6-0 |
| UTR Pro Florida | 2023/03/31 14:05 | Felipe Pinzon Moreno v Sean Daryabeigi | 2-6,3-6 |
| UTR Pro Florida | 2023/03/30 16:45 | Felipe Pinzon Moreno v Jean-Christian Morandais | 4-6,6-2,6-7 |
| UTR Pro Florida | 2023/03/28 19:51 | Felipe Pinzon Moreno v Marsel Ilhan | 4-6,4-6 |
| UTR Pro Florida | 2023/03/27 21:15 | Felipe Pinzon Moreno v Jesse Flores | 3-6,7-5,1-6 |
| ITF M25 Mosquera | 2023/03/21 16:10 | Tobias Franco v Felipe Pinzon Moreno | 6-7,6-3,10-7 |
| ITF M25 Mosquera | 2023/03/20 20:05 | Felipe Pinzon Moreno v Daniel Salazar | 5-7,6-3,10-5 |
| ITF M25 Anapoima | 2023/03/12 15:00 | Felipe Pinzon Moreno v Pedro Sakamoto | 4-6,7-5,7-10 |
| ITF M15 Naples | 2023/02/27 15:30 | Mac Kiger v Felipe Pinzon Moreno | 7-6,6-1 |