

Karen Khachanov defeated Daniil Medvedev 6-3 7-5 in the Monte Carlo Masters round of 16 on clay. The upset overturned the form book — Daniil Medvedev came in ranked #7, leading the head-to-head 7–1, defending last year's quarter-final. Karen Khachanov narrowed the head-to-head to 7–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-04-07 | Monte Carlo Masters | R64 | clay | Daniil Medvedev | 7-5 4-6 6-4 |
| 2025-02-17 | Doha | R32 | hard | Daniil Medvedev | 4-6 7-5 6-3 |
| 2023-10-23 | Vienna | QF | hard | Daniil Medvedev | 6-3 3-6 6-3 |
| 2023-03-20 | Miami Masters | SF | hard | Daniil Medvedev | 7-6 3-6 6-3 |
| 2023-01-02 | Adelaide 1 | QF | hard | Daniil Medvedev | 6-3 6-3 |
| 2019-08-05 | Canada Masters | SF | hard | Daniil Medvedev | 6-1 7-6 |
| 2018-10-15 | Moscow | SF | hard | Karen Khachanov | 6-1 6-7 6-3 |
| 2017-11-06 | NextGen Finals | RR | hard | Daniil Medvedev | 2-4 4-3 4-3 4-2 |
Averages over each player's completed matches in the selected window (142 vs 175). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Khachanov K.: 9 days rest · 1 match (14d) · Medvedev D.: 6 days rest · 1 match, 33 games (7d). Higher means fresher. About
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Per-surface Serve / Return Rating (0–100, percentile within the clay field, opponent-adjusted over 52 weeks). About