By surface
| Surface | Jessica Pegula | Madison Keys |
|---|---|---|
| Hard | 2 | 2 |
All meetings (4)
| Date | Tour | Tournament | Round | Surface | Winner | Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
|---|---|---|---|---|---|---|---|---|---|---|
| 2026-01-19 | WTA | Australian Open | Round of 16 | Hard | Jessica Pegula | 6-3 | 6-4 | |||
| 2025-01-06 | WTA | Adelaide | Final | Hard | Madison Keys | 3-6 | 6-4 | 1-6 | ||
| 2023-08-28 | WTA | US Open | Round of 16 | Hard | Madison Keys | 1-6 | 3-6 | |||
| 2022-10-10 | WTA | San Diego | Quarterfinal | Hard | Jessica Pegula | 6-4 | 7-5 |