Head to Head includes singles and doubles results.
| 08/30/19 | Andrew Bennett over Christian Waters | 6-4; 6-1 | Playoff Match |
| 08/09/19 | Christian Waters over Andrew Bennett |
2-6; 7-6; TB 11-9 |
|
| 07/26/19 | Andrew Bennett over Christian Waters | 6-1; 6-1 | |
| 11/04/18 | Andrew Bennett over Christian Waters |
3-6; 6-3; TB 10-5 |
Playoff Match |
