J. Pegula leads the head-to-head 6-4 since 2018 against C. Gauff, over 10 matches.
| Date | Winner | Score | Event |
| July 7, 2026 | C. Gauff | 2 - 1 | Wimbledon · Quarter-finals · grass |
| Nov. 2, 2025 | J. Pegula | 2 - 1 | Finals - Riyadh · hard |
| Oct. 12, 2025 | C. Gauff | 2 - 0 | Wuhan · Final · hard |
| Nov. 3, 2024 | C. Gauff | 2 - 0 | WTA Finals - Riyadh · hard |
| June 23, 2024 | J. Pegula | 2 - 0 | WTA Berlin · Semi-finals · grass |
| Nov. 5, 2023 | J. Pegula | 2 - 0 | WTA Finals - Cancun · Semi-finals · hard |
| Aug. 11, 2023 | J. Pegula | 2 - 1 | WTA Montreal · Quarter-finals · hard |
| June 29, 2023 | C. Gauff | 2 - 0 | WTA Eastbourne · Quarter-finals · grass |
| Feb. 14, 2022 | J. Pegula | 2 - 0 | Dubai · 1/16-finals · hard |
| Aug. 8, 2021 | J. Pegula | 2 - 1 | Exhibition Others matches |