A. Anisimova and M. Keys are level 1-1 in their head-to-head since 2018 over 2 matches.
| Surface | A. Anisimova | M. Keys |
|---|---|---|
| Grass | 0 | 1 |
| Hard | 1 | 0 |
| Date | Winner | Score | Event |
|---|---|---|---|
| July 4, 2026 | M. Keys | 2 - 1 | Wimbledon · 1/16-finals · grass |
| Nov. 3, 2025 | A. Anisimova | 2 - 1 | Finals - Riyadh · hard |