Head to Head includes singles and doubles results.
| 11/10/23 | Simon You over Anuj Tomar | 6-4; 1-6; 6-1 | Playoff Match |
| 09/17/23 | Anuj Tomar over Simon You | 7-5; 4-6; 7-5 | |
| 07/22/23 | Simon You over Anuj Tomar | 6-4; 6-3 | Playoff Match |
| 07/07/23 | Anuj Tomar over Simon You | 6-2; 4-6; 6-4 | |
| 04/30/23 | Anuj Tomar over Simon You | 5-7; 6-4; 7-6 |
