

Jannik Sinner defeated Karen Khachanov 5-7 6-3 6-3 in the Madrid Masters round of 16 on clay. The result followed the form book — Jannik Sinner came in ranked #1, leading the head-to-head 3–1. Jannik Sinner extended the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2024-01-15 | Australian Open | R16 | hard | Jannik Sinner | 6-4 7-5 6-3 |
| 2021-03-22 | Miami Masters | R32 | hard | Jannik Sinner | 4-6 7-6 6-4 |
| 2021-02-01 | Great Ocean Road Open | SF | hard | Jannik Sinner | 7-6 4-6 7-6 |
| 2020-08-31 | US Open | R128 | hard | Karen Khachanov | 3-6 6-7 6-2 6-0 7-6 |
Averages over each player's completed matches in the selected window (181 vs 142). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
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 clay field, opponent-adjusted over 52 weeks). About