Kei Nishikori defeated Karen Khachanov 6-7 6-2 6-2 in the Madrid Masters round of 64 on clay. The upset overturned the form book — Karen Khachanov came in ranked #26. Kei Nishikori extended the head-to-head to 5–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-05-18 | Geneva | R16 | clay | Karen Khachanov | 7-5 2-5 RET |
| 2024-12-30 | Hong Kong | R16 | hard | Kei Nishikori | 4-6 6-3 7-5 |
| 2021-05-31 | Roland Garros | R64 | clay | Kei Nishikori | 4-6 6-2 2-6 6-4 6-4 |
| 2018-10-22 | Vienna | R16 | hard | Kei Nishikori | 6-2 6-2 |
| 2018-06-18 | Halle | R16 | grass | Karen Khachanov | 6-2 6-2 |
| 2017-06-19 | Halle | R16 | grass | Karen Khachanov | 3-2 RET |
| 2016-08-29 | US Open | R64 | hard | Kei Nishikori | 6-4 4-6 6-4 6-3 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (116 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Khachanov K.: 10 days rest · 3 matches (14d). Higher means fresher. About