Head to Head includes singles and doubles results.
| 08/19/23 | Brian Determan over David Sherby | 7-5; 6-3 | |
| 04/23/23 | Brian Determan over David Sherby | 6-3; 6-3 | |
| 02/12/23 | Brian Determan over David Sherby | 7-6; 5-7; 6-4 | |
| 07/23/22 | Brian Determan over David Sherby | 6-1; 1-6; 6-2 | Playoff Match |
| 06/09/22 | Brian Determan over David Sherby | 6-1; 6-4 | |
| 01/19/22 | David Sherby over Brian Determan | 6-2; 6-0 | |
| 08/11/21 | David Sherby over Brian Determan | 6-3; 7-5 | |
| 03/27/21 | David Sherby over Brian Determan | 6-3; 0-6; 6-1 | |
| 01/12/21 | David Sherby over Brian Determan | 6-4; 6-0 | |
| 09/19/20 | Brian Determan over David Sherby | 5-7; 7-5; 7-5 | |
| 08/18/20 | Brian Determan over David Sherby |
2-6; 6-3; TB 10-6 |
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| 07/12/20 | Brian Determan over David Sherby | 7-6; 3-6; 6-0 | |
| 05/26/20 | Brian Determan over David Sherby | 7-6; 5-2 | |
| 03/01/20 | David Sherby over Brian Determan | 6-3; 7-5 | |
| 01/19/20 | David Sherby over Brian Determan | 7-5; 6-3 | |
| 12/29/19 | David Sherby over Brian Determan | 6-1; 6-3 | |
| 12/05/19 | Brian Determan over David Sherby | 1-6; 6-2; 7-5 | |
| 10/10/19 | David Sherby over Brian Determan | 3-6; 6-1; 6-3 | |
| 09/10/19 | David Sherby over Brian Determan | 6-3; 5-7 | |
| 05/26/19 | Brian Determan over David Sherby | 7-6; 7-6 | |
| 03/26/19 | Brian Determan over David Sherby | 6-1; 6-1 | |
| 03/13/19 | Brian Determan over David Sherby | 7-5; 6-2 | |
| 02/22/19 | David Sherby over Brian Determan | 6-4; 6-4 | |
| 01/20/19 | David Sherby over Brian Determan | 6-4; 7-5 | |
| 12/05/18 | Brian Determan over David Sherby | 6-0; 6-4 | |
| 11/07/18 | Brian Determan over David Sherby |
4-6; 6-4; TB 10-8 |
