Head to Head includes singles and doubles results.
| 11/09/23 | James Jones over Matt Heydinger | 7-5; 7-5 | |
| 08/01/23 | Matt Heydinger over James Jones | 6-3; 6-1 | Playoff Match |
| 07/15/23 | Matt Heydinger over James Jones | 6-4; 6-4 | |
| 06/01/23 | Matt Heydinger over James Jones | 6-4; 6-0 |
