Joao Sousa defeated Karen Khachanov 7-6 6-4 in the St. Petersburg round of 16 on carpet. The upset overturned the form book — Karen Khachanov came in leading the head-to-head 1–0, defending last year's round of 16. Joao Sousa claimed a first win over Karen Khachanov in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2016-09-26 | Chengdu | R32 | hard | Karen Khachanov | 7-6(3) 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.