Head to Head includes singles and doubles results.
| 08/29/19 | Christian Bruey over Craig Cimring | 6-3; 6-3 | Playoff Match |
| 08/16/19 | Craig Cimring over Christian Bruey | 7-5; 4-6; 6-4 | |
| 08/12/19 | Christian Bruey over Craig Cimring |
7-5; 6-7; TB 10-7 |
|
| 12/04/18 | Craig Cimring over Christian Bruey | 6-4; 7-6 |
