

Grigor Dimitrov defeated Karen Khachanov 6-7 6-4 7-6 in the Marseille semi-final on hard. Grigor Dimitrov extended the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-03-19 | Miami Masters | R32 | hard | Grigor Dimitrov | 6-7 6-4 7-5 |
| 2024-10-28 | Paris Masters | QF | hard | Karen Khachanov | 6-2 6-3 |
| 2023-10-02 | Shanghai Masters | R32 | hard | Grigor Dimitrov | 7-6 6-4 |
| 2021-11-01 | Paris Masters | R32 | hard | Grigor Dimitrov | 4-6 6-2 6-0 |
| 2020-10-26 | Vienna | R32 | hard | Grigor Dimitrov | 7-6 6-3 |
Averages over each player's completed matches in the selected window (114 vs 142). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Dimitrov G.: 6 days rest · 1 match, 26 games (7d) · Khachanov K.: 5 days rest · 1 match, 34 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 hard field, opponent-adjusted over 52 weeks). About