Head to Head includes singles and doubles results.
| 06/27/22 | Ashley Ruggirello over Jessica Brieske | 1-6; 6-4; 6-1 | Playoff Match |
| 09/08/21 | Ashley Ruggirello over Jessica Brieske | 6-4; 7-6 | Playoff Match |
| 08/17/21 | Jessica Brieske over Ashley Ruggirello | 6-1; 7-6 | |
| 09/26/19 | Ashley Ruggirello over Jessica Brieske | 0-0 No-Show | |
| 10/22/18 | Ashley Ruggirello over Jessica Brieske | 7-5; 6-4 | Playoff Match |
