Madison Keys leads 2 to 0 over 2 singles meetings since 2026. Last meeting on 25/06/2026 at Lexus Eastbourne Open - Eastbourne.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 25/06/2026 | Lexus Eastbourne Open - Eastbourne | Quarter-final | grass | Keys | 3-6 0-3 |
| 06/01/2026 | Brisbane International - Brisbane | Round 2 | hard | Keys | 4-6 3-6 |
| grass | Keys 1 - 0 Kessler |
| hard | Keys 1 - 0 Kessler |
| 2026 | Keys 2 - 0 Kessler |
165 wins, 90 losses since 2021 (64.7%).
Last matches: D V V D V
136 wins, 86 losses since 2021 (61.3%).
Last matches: D D D V D
Madison Keys leads 2 to 0 over 2 singles meetings since 2026.
On 25/06/2026, at Lexus Eastbourne Open - Eastbourne (Quarter-final): Madison Keys won 3-6 0-3.