Head to Head includes singles and doubles results.
| 10/16/22 | Joseph Millard over Ross Middleton | 6-1; 6-4 | Playoff Match |
| 08/21/22 | Joseph Millard over Ross Middleton | 6-2; 6-3 | |
| 07/13/21 | Joseph Millard over Ross Middleton |
4-6; 6-4; TB 10-3 |
|
| 07/15/20 | Joseph Millard over Ross Middleton | 6-3; 7-5 | |
| 09/16/19 | Joseph Millard over Ross Middleton |
7-6; 5-7; TB 10-5 |
|
| 08/25/19 | Ross Middleton over Joseph Millard |
7-6; 1-6; TB 10-7 |
|
| 07/31/19 | Joseph Millard over Ross Middleton |
6-3; 4-6; TB 10-7 |
