Head to Head includes singles and doubles results.
| 06/27/23 | Will Connelly over Trent Chaffee | 6-3; 6-2 | Playoff Match |
| 06/23/22 | Will Connelly over Trent Chaffee | 6-3; 6-3 | |
| 09/05/21 | Will Connelly over Trent Chaffee | 6-0; 6-4 | |
| 08/20/19 | Will Connelly over Trent Chaffee | 2-6; 7-6; 6-3 | Playoff Match |
