Head to Head includes singles and doubles results.
| 09/19/10 | Reagan McClymonds over David May | 4-6; 7-6; 7-6 | |
| 01/16/10 | David May over Reagan McClymonds | 6-1; 6-3 | |
| 08/02/09 | David May over Reagan McClymonds | 7-6; 6-7; 7-5 | |
| 07/16/09 | Reagan McClymonds over David May | 6-7; 7-5; 6-3 | |
| 03/21/09 | David May over Reagan McClymonds | 4-6; 6-4; 7-5 | |
| 12/19/08 | David May over Reagan McClymonds | 6-4; 3-6; 6-3 | |
| 11/12/08 | Reagan McClymonds over David May | 5-7; 6-3; 6-2 |
