

Alexander Zverev advanced when Karen Khachanov retired 7-5 3-0 in the Cincinnati Masters round of 16. Alexander Zverev extended the head-to-head to 6–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-07-27 | Canada Masters | SF | hard | Karen Khachanov | 6-3 4-6 7-6 |
| 2024-08-12 | Cincinnati Masters | R32 | hard | Alexander Zverev | 6-3 6-2 |
| 2024-03-18 | Miami Masters | R16 | hard | Alexander Zverev | 6-1 6-4 |
| 2021-07-24 | Tokyo Olympics | F | hard | Alexander Zverev | 6-3 6-1 |
| 2019-08-05 | Canada Masters | QF | hard | Karen Khachanov | 6-3 6-3 |
| 2018-10-29 | Paris Masters | QF | hard | Karen Khachanov | 6-1 6-2 |
| 2018-05-28 | Roland Garros | R16 | clay | Alexander Zverev | 4-6 7-6 2-6 6-3 6-3 |
| 2016-09-19 | St. Petersburg | R32 | carpet | Alexander Zverev | 7-6 6-4 |
Averages over each player's completed matches in the selected window (127 vs 82). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Zverev A.: 2 days rest · 2 matches, 53 games (7d) · Khachanov K.: 4 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