Head to Head includes singles and doubles results.
| 02/28/21 | Will Cunningham over Ray Gonzales | 6-4; 6-1 | |
| 12/05/20 | Ray Gonzales over Will Cunningham | 6-4; 6-3 | |
| 09/26/20 | Will Cunningham over Ray Gonzales | 6-2; 6-3 | |
| 06/14/20 | Ray Gonzales over Will Cunningham | 6-3; 6-3 |
