Head to Head includes singles and doubles results.
| 08/10/22 | Benjamin Kleinman over Jesse Wallin | 6-4; 0-6; 6-4 | Playoff Match |
| 12/11/21 | Benjamin Kleinman over Jesse Wallin | 6-2; 6-1 | |
| 11/02/21 | Jesse Wallin over Benjamin Kleinman | 6-4; 6-4 | Playoff Match |
| 08/28/21 | Jesse Wallin over Benjamin Kleinman | 10-8 | |
| 02/13/21 | Jesse Wallin over Benjamin Kleinman | 11-9; 4-6; 6-3 |
