Head to Head includes singles and doubles results.
| 05/20/23 | Charles Van Caloen over Devin Simmons | 6-0; 6-1 | Playoff Match |
| 01/23/23 | Charles Van Caloen over Devin Simmons | 6-1; 3-6; 6-4 | |
| 11/03/22 | Charles Van Caloen over Devin Simmons | 6-4; 6-0 | |
| 10/30/22 | Charles Van Caloen over Devin Simmons |
4-6; 6-1; TB 10-8 |
|
| 02/26/22 | Devin Simmons over Charles Van Caloen | 6-3; 6-4 | |
| 02/08/22 | Charles Van Caloen over Devin Simmons | 6-2; 7-5 |
