Head to Head includes singles and doubles results.
| 09/09/19 | Ben Holland over Barrie Stern | 6-1; 6-4 | |
| 07/10/19 | Barrie Stern over Ben Holland |
1-6; 6-3; TB 10-8 |
|
| 07/24/19 | Barrie Stern over Ben Holland | 7-6; 6-3 |
