| UTR Pro Florida | 2023/02/01 23:37 | Oliveira, Cristian v Isaiah Strode | 1-6,4-6 |
| UTR Pro Florida | 2023/01/31 20:00 | Oliveira, Cristian v Arthur Bonnaud | 1-6,2-5 |
| UTR Pro Florida | 2023/01/30 21:29 | Oliveira, Cristian v Leonardo Telles | 1-6,1-6 |
| UTR Pro Rio de Janeiro | 2023/01/04 12:00 | Oliveira, Cristian v Mason Meier | 6-2,6-4 |
| UTR Pro Rio de Janeiro | 2023/01/03 12:00 | Oliveira, Cristian v Obeid, Lucas | 6-4,6-0 |
| UTR Pro Rio de Janeiro | 2023/01/02 19:37 | Pedro Sakamoto v Oliveira, Cristian | 6-1,6-2 |
| ITF M25 Rio de Janeiro | 2022/10/20 15:50 | Oliveira, Cristian v Nicolas Zanellato | 1-6,2-6 |
| ITF M25 Rio de Janeiro | 2022/10/18 15:50 | Oliveira, Cristian v Gabriel Schenekenberg | 6-4,6-1 |
| UTR Pro Florida | 2023/02/01 23:22 | Leonardo Telles v Jackson Caldwell | 4-6,6-1,6-0 |
| UTR Pro Florida | 2023/01/30 22:50 | Arthur Bonnaud v Jackson Caldwell | 6-2,6-4 |
| UTR Pro Tennis Series Florida | 2022/11/30 20:00 | Mika Berghaus v Jackson Caldwell | 6-4,5-0 |
| UTR Pro Tennis Series Florida | 2022/11/28 16:00 | Nicolas H Cuesta v Jackson Caldwell | 6-1,6-1 |
| UTR Pro Tennis Series Florida | 2022/11/27 20:55 | Jackson Caldwell v Sallay, Peter | 6-1,4-6,6-6 |
| UTR Pro Tennis Series Texas | 2022/11/12 18:30 | Jackson Caldwell v Marson, Guido | 0-6,5-6 |
| UTR Pro Tennis Series Texas | 2022/11/11 14:30 | Jackson Caldwell v Stefan Storch | 4-6,7-6,5-0 |
| UTR Pro Tennis Series Texas | 2022/11/10 20:00 | Jackson Caldwell v Connor Smillie | 6-4,5-4 |