Head to Head includes singles and doubles results.
| 10/24/23 | Colin John over Caleb Zimmerman | 6-2; 6-3 | |
| 09/27/23 | Caleb Zimmerman over Colin John | 6-2; 6-2 | Playoff Match |
| 08/03/23 | Colin John over Caleb Zimmerman | 1-6; 7-6; 6-3 | |
| 05/03/23 | Caleb Zimmerman over Colin John | 6-4; 7-5 | |
| 01/29/23 | Caleb Zimmerman over Colin John | 6-2; 6-3 | |
| 10/26/22 | Caleb Zimmerman over Colin John | 6-4; 6-2 | |
| 07/07/22 | Caleb Zimmerman over Colin John | 6-3; 6-2 | |
| 05/02/22 | Caleb Zimmerman over Colin John | 6-2; 6-1 |
