Stan Wawrinka defeated Karen Khachanov 7-6 7-6 in the St. Petersburg round of 16 on carpet. The upset overturned the form book — Karen Khachanov came in ranked #15, leading the head-to-head 2–1. Stan Wawrinka narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2021-03-01 | Rotterdam | R32 | hard | Karen Khachanov | 6-4 7-5 |
| 2019-08-05 | Canada Masters | R32 | hard | Karen Khachanov | 6-4 6-7(3) 6-2 |
| 2018-12-31 | Doha | R32 | hard | Stan Wawrinka | 7-6(7) 6-4 |
Averages from each player's recent completed matches (19 vs 20). ATP, WTA & Challenger.