Head to Head includes singles and doubles results.
| 12/13/23 | Tom Cruickshank over Bo Jacober | 6-4; 7-6 | Playoff Match |
| 10/29/23 | Bo Jacober over Tom Cruickshank |
4-6; 7-6; TB 11-9 |
|
| 10/20/23 | Tom Cruickshank over Bo Jacober |
5-7; 7-6; TB 10-8 |
