Head to Head includes singles and doubles results.
| 01/17/24 | Jorge Jardines over Richard Bo Sharp | 5-7; 6-4; 7-6 | |
| 07/18/23 | Richard Bo Sharp over Jorge Jardines | 6-1; 2-6; 7-5 | |
| 05/13/23 | Richard Bo Sharp over Jorge Jardines | 3-6; 7-5; 6-3 | |
| 02/26/23 | Jorge Jardines over Richard Bo Sharp | 6-7; 6-3; 6-4 | Playoff Match |
| 01/18/23 | Richard Bo Sharp over Jorge Jardines | 7-5; 2-6; 6-4 | |
| 12/31/22 | Richard Bo Sharp over Jorge Jardines | 3-6; 6-1; 7-5 | |
| 12/29/22 | Jorge Jardines over Richard Bo Sharp | 7-5; 6-3 |
