Head to Head includes singles and doubles results.
| 08/08/19 | Matthew Gilbride over John Driscoll | 6-1; 6-2 | Playoff Match |
| 07/08/19 | Matthew Gilbride over John Driscoll | 6-1; 6-3 | |
| 10/23/18 | Matthew Gilbride over John Driscoll | 6-4; 6-4 | |
| 09/16/18 | John Driscoll over Matthew Gilbride | 6-7 Ret. |
