Head to Head includes singles and doubles results.
| 02/18/24 | David Ragan over Stephen Brinkman | 10-8 | |
| 08/09/23 | Stephen Brinkman over David Ragan | 6-1; 6-4 | |
| 01/12/23 | Stephen Brinkman over David Ragan | 7-6; 6-0 | |
| 08/29/21 | David Ragan over Stephen Brinkman | 6-4; 5-3 Ret. | |
| 09/01/18 | David Ragan over Stephen Brinkman | 6-0; 6-2 | |
| 05/13/18 | David Ragan over Stephen Brinkman | 6-2; 6-0 | |
| 03/15/18 | David Ragan over Stephen Brinkman | 6-4; 6-1 | |
| 12/17/17 | David Ragan over Stephen Brinkman | 6-0; 6-3 |
