| UTR Pro Florida | 2023/05/23 19:15 | Jackson Caldwell v Isaac Nortey | 3-6,3-6 |
| 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 | 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 | 2023/05/23 20:31 | Adit Sinha v Jake Fellows | 6-1,6-4 |
| UTR Pro Tennis Series Miami | 2021/11/07 13:00 | Wyatt DeMulling v Jake Fellows | 1-6,6-3,6-1 |
| UTR Pro Tennis Series Miami | 2021/11/06 19:30 | Jake Fellows v Geronimo E Busleiman | 2-6,4-5 |
| UTR Pro Tennis Series Miami | 2021/11/04 20:00 | Jake Fellows v Francisco Bastias | 6-0,1-6,1-6 |
| UTR Pro Tennis Series Miami | 2021/11/03 20:00 | Henry Lieberman v Jake Fellows | 7-6,5-3 |
| UTR Pro Tennis Series Miami | 2021/11/02 20:00 | Tyler Bowers v Jake Fellows | 5-7,3-5 |