Head to Head includes singles and doubles results.
| 12/09/23 | Stephen Dupuy over John Sullivan | 6-3; 6-3 | Playoff Match |
| 10/05/23 | John Sullivan over Stephen Dupuy | 6-7; 6-3; 6-1 | |
| 08/11/23 | John Sullivan over Stephen Dupuy |
6-4; 2-6; TB 10-6 |
|
| 08/09/23 | John Sullivan over Stephen Dupuy | 6-4; 6-4 |
