Head to Head includes singles and doubles results.
| 09/24/23 | Sundesh Raj over Chelsea Woodward | 6-4; 6-4 | Playoff Match |
| 08/20/23 | Sundesh Raj over Chelsea Woodward | 7-6; 6-2 | |
| 07/30/23 | Chelsea Woodward over Sundesh Raj | 0-0 No-Show |
