Head to Head includes singles and doubles results.
| 09/25/23 | Shawn Cole over Nathanael DeJonge | 6-2; 7-6 | |
| 11/20/22 | Nathanael DeJonge over Shawn Cole | 6-2; 6-3 | Playoff Match |
| 12/15/21 | Nathanael DeJonge over Shawn Cole |
1-6; 7-5; TB 10-8 |
