Head to Head includes singles and doubles results.
| 06/06/14 | Gerard Astrero ties Jon Flaherty | 1-1 Tie | |
| 05/29/14 | Gerard Astrero over Jon Flaherty | 6-4; 6-3 | |
| 04/28/14 | Gerard Astrero over Jon Flaherty | 10-8 | |
| 04/26/14 | Gerard Astrero over Jon Flaherty | 6-2; 7-6 | |
| 04/24/14 | Gerard Astrero over Jon Flaherty | 10-6 |
