Head to Head includes singles and doubles results.
| 07/25/18 | Jason Doctor over Darren Fleming | 7-6; 6-3 | |
| 03/12/18 | Jason Doctor over Darren Fleming | 7-6; 3-6; 6-2 | |
| 06/04/17 | Jason Doctor over Darren Fleming | 5-7; 6-2; 6-2 | |
| 06/04/16 | Jason Doctor over Darren Fleming | 6-3; 6-4 | Playoff Match |
| 04/17/16 | Darren Fleming over Jason Doctor | 6-4; 2-6; 6-4 | |
| 10/03/15 | Jason Doctor over Darren Fleming | 6-3; 4-6; 6-3 | |
| 07/03/15 | Jason Doctor over Darren Fleming | 6-2; 7-5 | |
| 04/30/15 | Jason Doctor over Darren Fleming |
7-6; 4-6; TB 11-9 |
