Head to Head includes singles and doubles results.
| 11/20/20 | Hewitt Strange over Nathan Dalechek | 6-2; 6-3 | Playoff Match |
| 10/22/20 | Nathan Dalechek over Hewitt Strange |
3-6; 6-3; TB 10-4 |
|
| 09/13/20 | Hewitt Strange over Nathan Dalechek | 6-3; 6-3 | |
| 08/17/20 | Nathan Dalechek over Hewitt Strange | 6-4; 6-1 |
