C. Gauff leads the head-to-head 6-1 since 2018 against B. Bencic, over 7 matches.
| Date | Winner | Score | Event |
| July 5, 2026 | C. Gauff | 2 - 1 | Wimbledon · 1/8-finals · grass |
| March 25, 2026 | C. Gauff | 2 - 1 | Miami · Quarter-finals · hard |
| Sept. 30, 2025 | C. Gauff | 2 - 1 | Beijing · 1/8-finals · hard |
| April 28, 2025 | C. Gauff | 2 - 0 | Madrid · 1/8-finals · clay |
| March 12, 2025 | B. Bencic | 2 - 1 | Indian Wells · 1/8-finals · hard |
| Jan. 19, 2025 | C. Gauff | 2 - 1 | Australian Open · 1/8-finals · hard |
| Aug. 5, 2023 | C. Gauff | 2 - 0 | WTA Washington · Quarter-finals · hard |