Daniil Medvedev leads the record after 9 meetings.
| Surface | Khachanov | Medvedev |
|---|---|---|
| Hard | 1 | 6 |
| Clay | 1 | 1 |
| Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|
| Monte-Carlo Rolex Masters - Monte-Carlo 2025 | R1 | Clay | Medvedev | 7-5 4-6 6-4 |
| Qatar ExxonMobil Open - Doha 2025 | R1 | Hard | Medvedev | 4-6 7-5 6-3 |
| Monte-Carlo Rolex Masters - Monte-Carlo 2024 | R3 | Clay | Khachanov | 6-3 7-5 |
| Erste Bank Open - Vienna 2023 | QF | Hard (Indoor) | Medvedev | 6-3 3-6 6-3 |
| Miami Open - Miami 2023 | SF | Hard | Medvedev | 7-6(5) 3-6 6-3 |
| Adelaide International 1 - Adelaide 2023 | QF | Hard | Medvedev | 6-3 6-3 |
| Coupe Rogers - Montreal 2019 | SF | Hard | Medvedev | 6-1 7-6(6) |
| Kremlin Cup - Moscow 2018 | SF | Hard (Indoor) | Khachanov | 6-1 6-7(5) 6-3 |
| Next Gen ATP Finals - Milan 2017 | R5 | Hard (Indoor) | Medvedev | 2-4 4-3(6) 4-3(3) 4-2 |
Meetings are the ones on our record. Older matches may be missing.
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