Head to Head includes singles and doubles results.
| 07/14/21 | Ben Orlando over Jordan Hendy | 7-5; 6-4 | Playoff Match |
| 06/16/21 | Jordan Hendy over Ben Orlando | 5-7; 6-3; 6-3 | |
| 05/30/21 | Jordan Hendy over Ben Orlando | 6-4; 4-6; 7-6 | |
| 05/14/21 | Jordan Hendy over Ben Orlando | 6-3; 6-3 | Playoff Match |
| 04/25/21 | Jordan Hendy over Ben Orlando | 6-3; 6-4 | |
| 04/13/21 | Jordan Hendy over Ben Orlando | 6-3; 4-6; 6-4 | |
| 03/11/20 | Jordan Hendy over Ben Orlando | 6-4; 6-4 |
